Heteroaryl azole compound and pest control agent

ABSTRACT

A heteroaryl azole compound of the following formula (II):an N-oxide compound, stereoisomer, tautomer or hydrate thereof, or a salt of any of these compounds. In the formula (II), R1 represents a substituted or unsubstituted C1-6 alkylthio group or the like; B1 represents a nitrogen atom or CR2; R2 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or the like; R3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or the like; R represents a substituted or unsubstituted C1-6 alkyl group or the like; A represents a carbon atom or a nitrogen atom; X represents a substituted or unsubstituted C1-6 alkyl group or the like; n represents a number of chemically acceptable X, and is an integer of 0 to 2; and X is the same or different when n is 2.

TECHNICAL FIELD

The present invention relates to a heteroaryl azole compound and a pest control agent. More specifically, the present invention relates to a heteroaryl azole compound that has excellent insecticidal activity and/or miticidal activity, is excellent in safety, and may be industrially advantageously synthesized, and a pest control agent containing the same as an active ingredient. The present application claims the priority of Japanese Patent Application No. 2018-164656 filed on 3 Sep., 2018, Japanese Patent Application No. 2018-223136 filed on 29 Nov., 2018, Japanese Patent Application No. 2018-240045 filed on filed on 21 Dec., 2018, and Japanese Patent Application No. 2019-061850 filed on 27 Mar., 2019, the contents of which are incorporated herein.

BACKGROUND ART

Various compounds having insecticidal or miticidal activity have been proposed. For practical use of such compounds as agrochemicals, it is required not only to have sufficiently high efficacy but to be less likely to cause chemical resistance, to cause neither phytotoxicity to plants nor soil pollution, and to be low toxic to livestock, fishes, etc.

Patent document 1 discloses a compound of formula (A), formula (B), etc.

PRIOR ART DOCUMENTS Patent Documents

-   Patent document 1: WO2016/012395

SUMMARY OF THE INVENTION Object to be Solved by the Invention

An object of the present invention is to provide a heteroaryl azole compound that is excellent in pest control activity, particularly, insecticidal activity and/or miticidal activity, is excellent in safety, and may be industrially advantageously synthesized. Another object of the present invention is to provide a pest control agent, an insecticide or acaricide, an ectoparasite control agent, or an endoparasite control agent or expellant containing the heteroaryl azole compound as an active ingredient.

Means to Solve the Object

As a result of diligent studies to attain the objects, the present invention including the following form has been completed.

-   [1] A compound of formula (II), an N-oxide compound, stereoisomer,     tautomer or hydrate thereof, or a salt of any of these compounds:

wherein

R¹ represents a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group or a substituted or unsubstituted C1-6 alkylsulfonyl group;

B¹ represents a nitrogen atom or CR²; R² represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted amino group, a cyano group or a halogeno group;

R³ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group;

R represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group;

A represents a carbon atom or a nitrogen atom;

X represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group;

n represents the number of chemically acceptable Xs, and is an integer of 0 to 2; and

Xs are the same or different when n is 2.

-   [2] The compound according to [1], an N-oxide compound,     stereoisomer, tautomer or hydrate thereof, or a salt of any of these     compounds, wherein in the formula (II), R represents a C1-6     haloalkyl group, a C1-6 haloalkoxy C1-6 haloalkyl group, a C2-6     haloalkenyl group or a C1-6 haloalkoxy C2-6 haloalkenyl group. -   [3] The compound according to [1], an N-oxide compound,     stereoisomer, tautomer or hydrate thereof, or a salt of any of these     compounds, wherein the formula (II) is the formula (IV):

wherein

R¹′ represents a substituted or unsubstituted C1-6 alkylsulfonyl group;

B¹′ represents a nitrogen atom or CR²′;

R²′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted amino group, a cyano group or a halogeno group;

R³′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group;

R′ represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group;

B²′ represents a nitrogen atom or CX¹′;

X¹′ represents a hydrogen atom, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group or a cyano group; and

x²′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group,

with the proviso that both X¹′ and X²′ are not hydrogen atoms at the same time.

-   [4] A pest control agent comprising at least one active ingredient     selected from the group consisting of a compound according to any     one of the above [1] to [3], an N-oxide compound, stereoisomer,     tautomer and hydrate thereof and a salt of any of these compounds. -   [5] An insecticide or acaricide comprising at least one active     ingredient selected from the group consisting of a compound     according to any one of the above [1] to [3], an N-oxide compound,     stereoisomer, tautomer and hydrate thereof and a salt of any of     these compounds. -   [6] An ectoparasite control agent comprising at least one active     ingredient selected from the group consisting of a compound     according to any one of the above [1] to [3], an N-oxide compound,     stereoisomer, tautomer and hydrate thereof and a salt of any of     these compounds. -   [7] An endoparasite control agent or expellant comprising at least     one active ingredient selected from the group consisting of a     compound according to any one of the above [1] to [3], an N-oxide     compound, stereoisomer, tautomer and hydrate thereof and a salt of     any of these compounds.

Effect of the Invention

The heteroaryl azole compound of the present invention of a salt thereof may control pests that are problems associated with crops or hygiene. Particularly, the heteroaryl azole compound of the present invention may effectively control agricultural insect pests and mites at a lower concentration. Furthermore, the heteroaryl azole compound of the present invention may effectively control ectoparasites and endoparasites harmful to humans and animals.

Mode of Carrying Out the Invention [Heteroaryl Azole Compound]

The heteroaryl azole compound of the present invention is a compound of formula (II) (hereinafter, also referred to as compound (II)), an N-oxide compound, stereoisomer, tautomer or hydrate thereof, or a salt of any of these compounds. The compound of formula (II) includes every stereoisomer which is an enantiomer or a diastereomer.

In the present invention, the term “unsubstituted” means a group consisting of only a mother nucleus. Only the name of a group consisting of a mother nucleus without the term “substituted” means an “unsubstituted” group unless otherwise specified.

On the other hand, the term “substituted” means that any hydrogen atom of a group consisting of a mother nucleus is substituted with a group (substituent) having a structure that is the same as or different from that of the mother nucleus. Thus, the “substituent” means another group bonded to the group consisting of a mother nucleus. The number of the substituent may be one or more. Two or more substituents are the same or different.

Terms such as “C1-6” mean that the number of carbon atoms in the group consisting of a mother nucleus is 1 to 6, etc. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified into a C2 alkoxy C4 alkyl group.

The “substituent” is not particularly limited as long as the substituent is chemically acceptable and produces the effect of the present invention. Hereinafter, a group capable of serving as the “substituent” is exemplified:

a C1-6 alkyl group such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group;

a C2-6 alkenyl group such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and a 2-methyl-2-propenyl group;

a C2-6 alkynyl group such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1-methyl-2-propynyl group;

a C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cubanyl group;

a C6-10 aryl group such as a phenyl group and a naphthyl group;

a C6-10 aryl C1-6 alkyl group such as a benzyl group and a phenethyl group;

a 3- to 6-membered heterocyclyl group;

a 3- to 6-membered heterocyclyl C1-6 alkyl group;

a hydroxy group;

a C1-6 alkoxy group such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group;

a C2-6 alkenyloxy group such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group;

a C2-6 alkynyloxy group such as an ethynyloxy group and a propargyloxy group;

a C6-10 aryloxy group such as a phenoxy group and a naphthoxy group;

a C6-10 aryl C1-6 alkoxy group such as a benzyloxy group and a phenethyloxy group;

a 5- or 6-membered heteroaryloxy group such as a thiazolyloxy group and a pyridyloxy group;

a 5- or 6-membered heteroaryl C1-6 alkyloxy group such as a thiazolylmethyloxy group and a pyridylmethyloxy group;

a formyl group;

a C1-6 alkylcarbonyl group such as an acetyl group and a propionyl group;

a formyloxy group;

a C1-6 alkylcarbonyloxy group such as an acetyloxy group and a propionyloxy group;

a C6-10 arylcarbonyl group such as a benzoyl group;

a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, a n-butoxycarbonyl group, and a t-butoxycarbonyl group;

a C1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, a n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group;

a carboxy group;

a halogeno group such as a fluoro group, a chloro group, a bromo group, and an iodo group;

a C1-6 haloalkyl group such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group, and a 2,4,6-trichlorohexyl group;

a C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group;

a C2-6 haloalkynyl group such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group;

a C1-6 haloalkoxy group such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group;

a C2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group;

a C1-6 haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group, and a trichioroacetyl group;

an amino group;

a C1-6 alkyl-substituted amino group such as a methylamino group, a dimethylamino group, and a diethylamino group;

a C6-10 arylamino group such as an anilino group and a naphthylamino group;

a C6-10 aryl C1-6 alkylamino group such as a benzylamino group and a phenethylamino group;

a formylamino group;

a C1-6 alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group, and an i-propylcarbonylamino group;

a C1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, a n-propoxycarbonylamino group, and an i-propoxycarbonylamino group;

an unsubstituted or substituted aminocarbonyl group such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, and a N-phenyl-N-methylaminocarbonyl group;

an imino C1-6 alkyl group such as an iminomethyl group, a (1-imino)ethyl group, and a (1-imino)-n-propyl group;

a substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as a N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino) ethyl group, a (1-(N-hydroxy)-imino)propyl group, a N-methoxy-iminomethyl group, and a (1-(N-methoxy)-imino)ethyl group;

a C1-6 alkoxyimino group such as a methoxyimino group, an ethoxyimino group, a n-propoxyimino group, an i-propoxyimino group, and a n-butoxyimino group; an aminocarbonyloxy group;

a C1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group; a mercapto group;

a C1-6 alkylthio group such as a methylthio group, an ethylthio group, a n-propylthio group, an i-propylthio group, a n-butylthio group, an i-butylthio group, a s-butylthio group, and a t-butylthio group;

a C1-6 haloalkylthio group such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group;

a C6-10 arylthio group such as a phenylthio group and a naphthylthio group;

a 5- or 6-membered heteroarylthio group such as a thiazolylthio group and a pyridylthio group;

a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group;

a C1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group;

a C6-10 arylsulfinyl group such as a phenylsulfinyl group;

a 5- or 6-membered heteroarylsulfinyl group such as a thiazolylsulfinyl group and a pyridylsulfinyl group;

a C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group;

a C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group;

a C6-10 arylsulfonyl group such as a phenylsulfonyl group;

a 5- or 6-membered heteroarylsulfonyl group such as a thiazolylsulfonyl group and a pyridylsulfonyl group;

a C1-6 alkylsulfonyloxy group such as a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group;

a C1-6 haloalkylsulfonyloxy group such as a trifluoromethylsulfonyloxy group and a 2,2,2-trifluoroethylsulfonyloxy group;

a tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group;

a tri-C6-10 aryl-substituted silyl group such as a triphenylsilyl group;

a cyano group;

and a nitro group.

For these “substituents”, any hydrogen atom in each substituent may be substituted with a group having a distinct structure. In this case, as the “substituent”, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group or the like may be exemplified.

The “3- to 6-membered heterocyclyl group” described above contains 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. The heterocyclyl group may be either monocyclic or polycyclic. The polycyclic heterocyclyl group has at least one hetero ring, and the remaining ring(s) may be any of a saturated alicyclic ring, an unsaturated alicyclic ring and an aromatic ring. As the “3- to 6-membered heterocyclyl group”, a 3- to 6-membered saturated heterocyclyl group, a 5- or 6-membered heteroaryl group, a 5- or 6-membered partially unsaturated heterocyclyl group or the like may be exemplified.

As the 3- to 6-membered saturated heterocyclyl group, an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group or the like may be exemplified.

As the 5-membered heteroaryl group, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group or the like may be exemplified.

As the 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group or the like may be exemplified.

[B¹]

In the formula (II), B¹ represents a nitrogen atom or CR².

Specifically, the compound of formula (II) is a compound of formula (I) or formula (III).

In the formula (I), R¹, R², R³, R, A, X and n represent the same meanings as described in the formula (II). In the formula (III), R¹, R³, R, A, X and n represent the same meanings as described in the formula (II).

[A]

In the formula (II), A represents a carbon atom or a nitrogen atom.

Specifically, the compound of formula (II) is a compound of the following formula (II-1) or formula (II-2).

In the formula (II-1) and the formula (II-2), R¹, R³ R, B¹, X and n represent the same meanings as described in the formula (II).

The compound of formula (II) is preferably a compound of formula (II-1).

Specifically, the compound of formula (II) is a compound of the following formula (I-1), formula (I-2), formula (III-1) or formula (III-2).

In the formula (I-1) and the formula (I-2), R¹, R², R³, R, X and n represent the same meanings as described in the formula (II). In the formula (III-1) and the formula (III-2), R¹, R³, R, X and n represent the same meanings as described in the formula (II).

The compound of formula (II) is preferably a compound of formula (I-1), the formula (III-1) or the formula (III-2), more preferably a compound of formula (I-1) or the formula (III-1).

[R¹]

In the formula (II), R¹ represents a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group or a substituted or unsubstituted C1-6 alkylsulfonyl group.

As the “C1-6 alkylthio group” represented by R¹, a methylthio group, an ethylthio group, a n-propylthio group, a n-butylthio group, a n-pentylthio group, a n-hexylthio group, an i-propylthio group, an i-butylthio group or the like may be exemplified.

As the “C1-6 alkylsulfinyl group” represented by R¹, a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group or the like may be exemplified.

As the “C1-6 alkylsulfonyl group” represented by R¹, a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group or the like may be exemplified.

As the substituents on the “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” and the “C1-6 alkylsulfonyl group” represented by R¹, a halogeno group such as a fluoro group, a chloro group, a bromo group, and an iodo group may be preferably exemplified.

R¹ is preferably a C1-6 alkylsulfonyl group.

[R²]

In the formula (II), R² represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted amino group, a cyano group or a halogen group.

The “C1-6 alkyl group” represented by R² may be linear or branched. As the “C1-6 alkyl group”, a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, an i-propyl group, an i-butyl group, a s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group or the like may be exemplified.

As the “C2-6 alkenyl group” represented by R², a vinyl group, a 1-methylvinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group or the like may be exemplified.

As the “C2-6 alkynyl group” represented by R², an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, a 1,1-dimethyl-2-butynyl group or the like may be exemplified.

As the substituents on the “C1-6 alkyl group”, the “C2-6 alkenyl group” and the “C2-6 alkynyl group” represented by R², halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group may be preferably exemplified.

The “substituted or unsubstituted amino group” represented by R² is a group represented by “—NR^(a)R^(b)”. As R^(a) and R^(b) in the formula, each independently, a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, a group represented by “—C(═NH)NR^(f)R^(g)”, or the like may be exemplified.

As the “C1-6 alkyl group” represented by each of R^(a) and R^(b), the same group as exemplified for R² above is exemplified.

As the “C1-6 alkylcarbonyl group” represented by each of R^(a) and R^(b), an acetyl group, a propionyl group or the like may be exemplified.

As the “substituted or unsubstituted aminocarbonyl group” represented by each of R^(a) and R^(b), an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group or the like may be exemplified.

R^(f) and R^(g) in the group represented by “—C(═NH)NR^(f)R^(g)” represented by each of R^(a) and R^(b) each independently represent a hydrogen atom, a C1-6 alkyl group, a formyl group or a C1-6 alkylcarbonyl group.

As the “C1-6 alkyl group” represented by each of R^(f) and R^(g), the same group as exemplified for R² above is exemplified. As the “C1-6 alkylcarbonyl group” represented by each of R^(f) and R^(g), the same group as exemplified for each of R^(a) and R^(b) above is exemplified.

As the “halogeno group” represented by R², a fluoro group, a chloro group, a bromo group, an iodo group or the like may be exemplified.

R² is preferably a hydrogen atom, a C1-6 alkyl group or a halogeno group.

[R³]

In the formula (II), R³ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group.

As the “substituted or unsubstituted C1-6 alkyl group” and the “halogeno group” represented by R³, the same groups as exemplified for R² above are exemplified.

R³ is preferably a hydrogen atom.

[R]

In the formula (II), R represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

As the “C1-6 alkyl group”, the “C2-6 alkenyl group” and the “C2-6 alkynyl group” represented by R, the same groups as exemplified for R² above are exemplified.

As the “substituted C1-6 alkyl group” represented by R, a C1-6 haloalkyl group such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoromethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,4,4,4-hexafluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a 2,2,3,3,4,4,5,5-octafluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group or a 2,4,6-trichlorohexyl group; a C1-6 haloalkoxy C1-6 haloalkyl group such as a 1,1,2-trifluoro-2-(trifluoromethoxy)ethyl group or a 1,1,2-trifluoro-2-(perfluoropropoxy)ethyl group; or a benzyl group may be exemplified.

As the “substituted C2-6 alkenyl group” represented by R, a C2-6 haloalkenyl group such as a 2-fluoro-2-bromovinyl group, a 2,2-dichlorovinyl group, a 2-chloro-2-iodovinyl group, a 2-chloro-1-propenyl group, a 2,3,3,3-tetrafluoro-1-propenyl group, a 3,3,3-trifluoro-1-propenyl group, a 2-chloro-3,3,3-trifluoro-1-propenyl group, a 3,3,3-trifluoro-2-trifluoromethyl-1-propenyl group, a 2-fluoro-1-butenyl group, a 3,3,4,4,4-pentafluoro-1-butenyl group, 2,3,4,4,4-pentafluoro-1-butenyl group, a 2,3,3,4,4,4-hexafluoro-1-butenyl group, a 2-chloro-3,3,4,4,4-pentafluoro-1-butenyl group, 2,3,3,4,4,5,5-heptafluoro-1-pentenyl group, a 3,3,4,4,5,5,5-heptafluoro-1-pentenyl group, a 2-chloro-3,3,4,4,5,5,5-heptafluoro-1-pentenyl group, a 2,3,3,4,4,5,5,5-octafluoro-1-pentenyl group, and a 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexenyl group; and a C1-6 haloalkoxy C2-6 haloalkenyl group such as a 1,2-difluoro-2-(perfluoropropoxy)vinyl group may be exemplified.

As the substituents on the “C1-6 alkyl group”, the “C2-6 alkenyl group” and the “C2-6 alkynyl group” represented by R, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; and C1-6 haloalkoxy groups such as a trifluoromethoxy group, a perfluoroethoxy group, a 2-chloro-n-propoxy group, a perfluoropropoxy group and a 2,3-dichlorobutoxy group may be preferably exemplified.

The “C6-10 aryl group” represented by R may be either monocyclic or polycyclic. The polycyclic aryl group has at least one aromatic ring, and the remaining ring(s) may be any of a saturated alicyclic ring, an unsaturated alicyclic ring and an aromatic ring. As the “C6-10 aryl group”, a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, a tetralinyl group or the like is exemplified.

As the “5- to 6-membered heteroaryl group” represented by R, a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an isothiazolyl group, a triazolyl group (specifically, a [1,2,3]triazolyl group or a [1,2,4]triazolyl group), an oxadiazolyl group (specifically, a [1,2,3]oxadiazolyl group, a [1,2,4]oxadiazolyl group, a [1,2,5]oxadiazolyl group or a [1,3,4]oxadiazolyl group), a thiadiazolyl group or a tetrazolyl group; or a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group or a triazinyl group may be exemplified.

As the substituents on the “C6-10 aryl group” and the “5- to 6-membered heteroaryl group” represented by R, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group and a n-hexyl group; C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group and a 2,4,6-trichlorohexyl group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group; C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, a trifluoromethoxy group and a 1,1,2,2-tetrafluoroethoxy group; and C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group may be exemplified.

R in the formula (II) is preferably a C1-6 haloalkyl group, a C1-6 haloalkoxy C1-6 haloalkyl group, a C2-6 haloalkenyl group or a C1-6 haloalkoxy C2-6 haloalkenyl group.

[X]

In the formula (II), X is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group.

As the “substituted or unsubstituted C1-6 alkyl group”, the “substituted or unsubstituted C2-6 alkenyl group”, the “substituted or unsubstituted C2-6 alkynyl group”, the “substituted or unsubstituted amino group” and the “halogeno group” represented by X, the same groups as exemplified for R² above are exemplified.

As the “substituted or unsubstituted C1-6 alkylthio group”, the “substituted or unsubstituted C1-6 alkylsulfinyl group” and the “substituted or unsubstituted C1-6 alkylsulfonyl group” represented by X, the same groups as exemplified for R² above are exemplified.

As the “substituted or unsubstituted C6-10 aryl group” and the “substituted or unsubstituted 5- to 6-membered heteroaryl group”, the same groups as exemplified for R above are exemplified.

As the “C1-6 alkoxy group” represented by X, a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, a t-butoxy group or the like may be exemplified.

As the “C1-6 alkoxycarbonyl group” represented by X, a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, a n-butoxycarbonyl group, a t-butoxycarbonyl group or the like may be exemplified.

As the substituent on the “C1-6 alkyl group” represented by X, a halogeno group such as a fluoro group, a chloro group, a bromo group or an iodo group; a C1-6 alkoxy group such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group or a t-butoxy group; or a C1-6 alkoxyimino group such as a methoxyimino group, an ethoxyimino group, a n-propoxyimino group, an i-propoxyimino group or a n-butoxyimino group may be preferably exemplified.

As the substituents on the “C2-6 alkenyl group”, the “C2-6 alkynyl group”, the “C1-6 alkoxy group”, the “C1-6 alkylthio group”, the “C1-6 alkylsulfinyl group” and the “C1-6 alkylsulfonyl group” represented by X, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; and C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group may be preferably exemplified.

As the “C3-8 cycloalkyl group” represented by X, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cubanyl group or the like may be exemplified.

As the “C6-10 aryloxy group” represented by X, a phenoxy group, a naphthyloxy group or the like may be exemplified.

As the “5- to 6-membered heteroaryloxy group” represented by X, a pyridyloxy group, a pyrimidyloxy group or the like may be exemplified.

The substituents on the “C3-8 cycloalkyl group”, the “C6-10 aryl group”, the “5- to 6-membered heteroaryl group”, the “C6-10 aryloxy group” and the “5- to 6-membered heteroaryloxy group” represented by X, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group and a n-hexyl group; C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group and a 2,4,6-trichlorohexyl group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group; and C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group may be preferably exemplified, and halogeno groups or C1-6 alkyl groups are more preferable.

As the “substituted or unsubstituted aminocarbonyl group” represented by X, the same group as exemplified for R^(a) and R^(b) above is exemplified.

The “substituted or unsubstituted hydrazinyl group” represented by X is a group represented by the formula (a).

In the formula (a), * represents a binding position, R^(c), R^(d) and R^(e) each independently represent a hydrogen atom, a C1-6 alkyl group, a substituted or unsubstituted phenylsulfonyl group or the like.

As the “C1-6 alkyl group” represented by each of R^(c), R^(d) and R^(e), the same group as exemplified for X above is exemplified.

As the “substituted phenylsulfonyl group” represented by R^(c), R^(d) and R^(e), a paratoluenesulfonyl group or the like may be exemplified.

X is preferably a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group or a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, more preferably a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

[n]

n represents a number of chemically acceptable X, and is an integer of 0 to 2; and X is the same or different when n is 2.

n is preferably 0 to 1.

[Salt]

The salt of the compound (II) is not particularly limited as long as the salt is agriculturally or horticulturally acceptable. As the salt of the compound (I), for example, a salt of an inorganic acid such as hydrochloric acid and sulfuric acid; a salt of an organic acid such as acetic acid and lactic acid; a salt of an alkali metal such as lithium, sodium and potassium; a salt of an alkaline earth metal such as calcium and magnesium; a salt of a transition metal such as iron and copper; a salt of an organic base such as triethylamine, tributylamine, pyridine, and hydrazine; ammonia; or the like may be exemplified.

[Production Method]

The method for producing the compound (II) or the salt of the compound (II) is not particularly limited. For example, the compound (II) or the salt of the compound (II) of the present invention may be obtained by known methods described in Examples, etc. Alternatively, the salt of the compound (II) may be obtained by a known approach from the compound (II).

[Compound of formula (IV)]

The compound of formula (II) is preferably a compound of formula (IV).

wherein

R¹′ represents a substituted or unsubstituted C1-6 alkylsulfonyl group;

B¹′ represents a nitrogen atom or CR²′; R²′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted amino group, a cyano group or a halogeno group;

R³′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group; R′ represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group;

B²′ represents a nitrogen atom or CX¹′;

X¹′ represents a hydrogen atom, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group or a cyano group; and

X²′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group,

with the proviso that both X¹′ and X²′ are not hydrogen atoms at the same time.

[B¹]

In the formula (IV), B¹′ represents a nitrogen atom or CR²′.

Specifically, the compound of formula (IV) is a compound of formula (IV-1) or the formula (IV-2).

In the formula (IV-1), R¹′, R²′, R³′, R′, B²′, X¹′ and X²′ represent the same meanings as described in the formula (IV). In the formula (IV-2), R¹′, R³′, R′, B²′, X¹′ and X²′ represent the same meanings as described in the formula (IV).

[R¹′]

In the formula (IV), R¹′ represents a substituted or unsubstituted C1-6 alkylsulfonyl group.

As the “C1-6 alkylsulfonyl group” represented by R¹′, a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group or the like may be exemplified.

As the substituent on the “C1-6 alkylsulfonyl group” represented by R¹′, a halogeno group such as a fluoro group, a chloro group, a bromo group or an iodo group may be preferably exemplified.

R¹′ is preferably a C1-6 alkylsulfonyl group.

[R²′]

In the formula (IV), R²′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted amino group, a cyano group or a halogeno group.

The “C1-6 alkyl group” represented by R²′ may be linear or branched. As the “C1-6 alkyl group”, a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, an i-propyl group, an i-butyl group, a s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group or the like may be exemplified.

As the “C2-6 alkenyl group” represented by R²′, a vinyl group, a 1-methylvinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group or the like may be exemplified.

As the “C2-6 alkynyl group” represented by R²′, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, a 1,1-dimethyl-2-butynyl group or the like may be exemplified.

As the substituents on the “C1-6 alkyl group”, the “C2-6 alkenyl group” and the “C2-6 alkynyl group” represented by R²′, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group may be preferably exemplified.

The “substituted or unsubstituted amino group” represented by R^(v) is a group represented by “—NR^(a)R^(b)”. As R^(a) and R^(b) in the formula, each independently, a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group or the like may be exemplified.

As the “C1-6 alkyl group” represented by each of R^(a) and R^(b), the same group as exemplified for R²′ above is exemplified.

As the “C1-6 alkylcarbonyl group” represented by each of R^(a) and R^(b), an acetyl group, a propionyl group or the like may be exemplified.

As the “substituted or unsubstituted aminocarbonyl group” represented by each of R^(a) and R^(b), an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group or the like may be exemplified.

As the “halogeno group” represented by R²′, a fluoro group, a chloro group, a bromo group, an iodo group or the like may be exemplified.

R²′ is preferably a hydrogen atom, a C1-6 alkyl group or a halogeno group.

[R³′]

In the formula (IV), R³ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group.

As the “substituted or unsubstituted C1-6 alkyl group” and the “halogeno group” represented by R³′, the same groups as exemplified for R²′ above are exemplified.

R³′ is preferably a hydrogen atom. In the formula (IV), R′ represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

The “C6-10 aryl group” represented by R′ may be either monocyclic or polycyclic. The polycyclic aryl group has at least one aromatic ring, and the remaining ring(s) may be any of a saturated alicyclic ring, an unsaturated alicyclic ring and an aromatic ring. As the “C6-10 aryl group”, a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, a tetralinyl group or the like is exemplified.

As the “5- to 6-membered heteroaryl group” represented by R′, a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an isothiazolyl group, a triazolyl group (specifically, a [1,2,3]triazolyl group or a [1,2,4]triazolyl group), an oxadiazolyl group (specifically, a [1,2,3]oxadiazolyl group, a [1,2,4]oxadiazolyl group, a [1,2,5]oxadiazolyl group or a [1,3,4]oxadiazolyl group), a thiadiazolyl group or a tetrazolyl group; or a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group or a triazinyl group may be exemplified.

As the substituents on the “C6-10 aryl group” and the “5- to 6-membered heteroaryl group” represented by R′, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group and a n-hexyl group; C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl roup, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group and a 2,4,6-trichlorohexyl group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group; C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, a trifluoromethoxy group and a 1,1,2,2-tetrafluoroethoxy group; and C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group may be preferably exemplified, and C1-6 haloalkyl groups and C1-6 haloalkoxy groups may be more preferably exemplified.

R′ is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group, more preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group.

[B²′]

In the formula (IV), B²′ represents a nitrogen atom or CX¹′.

Specifically, the compound of formula (IV) is a compound of formula (IV-3) or the formula (IV-4).

In the formula (IV-3), R¹′, R³′, R′, B¹′, X¹′ and X²′ represent the same meanings as described in the formula (IV). In the formula (IV-4), R¹′, R³′, R′, B¹′ and X²′ represent the same meanings as described in the formula (IV).

Specifically, the compound of formula (IV) is a compound of formula (IV-5), the formula (IV-6), the formula (IV-7) or the formula (IV-8).

In the formula (IV-5), R¹′, R²′, R³′, R′, X¹′ and X²′ represent the same meanings as described in the formula (IV). In the formula (IV-6), R¹′, R³′, R′, X¹′ and X²′ represent the same meanings as described in the formula (IV). In the formula (IV-7), R¹′, R²′, R³′, R′ and X²′ represent the same meanings as described in the formula (IV). In the formula (IV-8), R¹′, R³′, R′ and X²′ represent the same meanings as described in the formula (IV).

The compound of formula (IV) is preferably a compound of formula (IV-5) or the formula (IV-6).

The compound of formula (IV) is preferably a compound of formula (IV-8).

In the formula (IV), X¹′ represents a hydrogen atom, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group or a cyano group.

As the “substituted or unsubstituted C1-6 alkylsulfonyl group” represented by X¹′, the same group as exemplified for R¹′ above is exemplified.

As the “substituted or unsubstituted C2-6 alkenyl group”, the “substituted or unsubstituted C2-6 alkynyl group” and the “substituted or unsubstituted amino group” represented by X¹′, the same groups as exemplified for R²′ above are exemplified.

As the “substituted or unsubstituted C6-10 aryl group” and the “substituted or unsubstituted 5- to 6-membered heteroaryl group” represented by X¹′, the same groups as exemplified for R′ above are exemplified.

As the “C1-6 alkoxy group” represented by X¹′, a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, a t-butoxy group or the like may be exemplified.

As the “C1-6 alkoxycarbonyl group” represented by X¹′, a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, a n-butoxycarbonyl group, a t-butoxycarbonyl group or the like may be exemplified.

As the “C1-6 alkylthio group” represented by X¹′, a methylthio group, an ethylthio group, a n-propylthio group, a n-butylthio group, a n-pentylthio group, a n-hexylthio group, an i-propylthio group, an i-butylthio group or the like may be exemplified.

As the “C1-6 alkylsulfinyl group” represented by X¹′, a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group or the like may be exemplified.

As the substituents on the “C1-6 alkoxy group”, the “C1-6 alkoxycarbonyl group”, the “C1-6 alkylthio group”, the “C1-6 alkylsulfinyl group” and the “C1-6 alkylsulfonyl group” represented by X¹′, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; and C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group may be preferably exemplified.

As the “C3-8 cycloalkyl group” represented by X¹′, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cubanyl group or the like may be exemplified.

As the “C6-10 aryloxy group” represented by X¹′, a phenoxy group, a naphthyloxy group or the like may be exemplified.

As the “5- to 6-membered heteroaryloxy group” represented by X¹′, a pyridyloxy group, a pyrimidyloxy group or the like may be exemplified.

As the substituents on the “C3-8 cycloalkyl group”, the “C6-10 aryl group”, the “5- to 6-membered heteroaryl group”, the “C6-10 aryloxy group” and the “5- to 6-membered heteroaryloxy group” represented by X¹′, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group and a n-hexyl group; C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group and a 2,4,6-trichlorohexyl group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group; and C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group may be preferably exemplified, and C1-6 alkyl groups are more preferable.

As the “substituted or unsubstituted aminocarbonyl group” represented by X¹′, the same group as exemplified for R^(a) and R^(b) above is exemplified.

The “substituted or unsubstituted hydrazinyl group” represented by X¹′ is a group represented by the formula (a).

In the formula (a), * represents a binding position, R^(c), R^(d) and R^(e) each independently represent a hydrogen atom, a C1-6 alkyl group or a substituted or unsubstituted phenylsulfonyl group.

As the “C1-6 alkyl group” represented by each of R^(c), R^(d) and R^(e), the same group as exemplified for X above is exemplified.

As the “substituted phenylsulfonyl group” represented by each of R^(c), R^(d) and R^(e), a paratoluenesulfonyl group or the like may be exemplified.

X¹′ is preferably a hydrogen atom, a C2-6 alkenyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

[X²′]

In the formula (II), X²′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group.

As the “substituted or unsubstituted C1-6 alkyl group” and the “halogeno group” represented by X²′, the same groups as exemplified for R²′ above are exemplified.

As the “substituted or unsubstituted C1-6 alkylsulfonyl group” represented by X²′, the same group as exemplified for R¹′ above is exemplified.

As the “substituted or unsubstituted C6-10 aryl group” and the “substituted or unsubstituted 5- to 6-membered heteroaryl group” represented by X²′, the same groups as exemplified for R′ above are exemplified.

As the “substituted or unsubstituted aminocarbonyl group” represented by X²′, the same group as exemplified for R^(a) and R^(b) is exemplified.

As the “substituted or unsubstituted C2-6 alkenyl group”, the “substituted or unsubstituted C2-6 alkynyl group”, the “substituted or unsubstituted C1-6 alkoxy group”, the “substituted or unsubstituted C1-6 alkoxycarbonyl group”, the “substituted or unsubstituted C1-6 alkylthio group”, the “substituted or unsubstituted C1-6 alkylsulfinyl group”, the “substituted or unsubstituted C3-8 cycloalkyl group”, the “substituted or unsubstituted C6-10 aryloxy group”, the “substituted or unsubstituted 5- to 6-membered heteroaryloxy group”, the “substituted or unsubstituted amino group” and the “substituted or unsubstituted hydrazinyl group” represented by X²′, the same groups as exemplified for X¹′ above are exemplified.

X²′ is preferably a hydrogen atom, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted amino group or a halogeno group, more preferably a hydrogen atom or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

It is to be noted that both X¹′ and X²′ are not hydrogen atoms at the same time.

The heteroaryl azole compound of the present invention is excellent in control effect on pests such as various agricultural insect pests and mites affecting the growth of plants.

Also, the heteroaryl azole compound of the present invention is a highly safe substance because of less phytotoxicity to crops and low toxicity to fishes and warm-blooded animals. Hence, the heteroaryl azole compound of the present invention is useful as an active ingredient for insecticides or acaricides.

Furthermore, in recent years, many insect pests such as diamondback moth, white-backed plant hopper, leafhopper, and aphid have developed resistance to various existing chemicals, causing problems of insufficient efficacy of these chemicals. Thus, chemicals effective for insect pests of resistant strains have been desired. The heteroaryl azole compound of the present invention exhibits an excellent control effect not only on sensitive strains but also on insect pests of various resistant strains and even mites of acaricide-resistant strains.

The heteroaryl azole compound of the present invention is excellent in control effect on ectoparasites and endoparasites harmful to humans and animals. Also, the heteroaryl azole compound of the present invention is a highly safe substance because of low toxicity to fishes and warm-blooded animals. Hence, the heteroaryl azole compound of the present invention is useful as an active ingredient for ectoparasite and endoparasite control agents.

The heteroaryl azole compound of the present invention exhibits efficacy at every developmental stage of organisms to be controlled, and exhibits an excellent control effect on, for example, eggs, nymphs, larvae, pupae, and adults of mites, insects, and the like.

[Pest Control Agent]

The pest control agent of the present invention contains at least one active ingredient selected from the heteroaryl azole compounds of the present invention. The amount of the heteroaryl azole compound contained in the pest control agent of the present invention is not particularly limited as long as its pest control effect is exhibited. The pest control agent is an agent controlling pests and includes an insecticide or acaricide, an ectoparasite control agent, or an endoparasite control agent or expellant, or the like.

[Insecticide or Acaricide]

The insecticide or acaricide of the present invention contains at least one active ingredient selected from the heteroaryl azole compounds of the present invention. The amount of the heteroaryl azole compound contained in the insecticide or acaricide of the present invention is not particularly limited as long as its insecticidal or miticidal effect is exhibited.

The pest control agent or the insecticide or acaricide of the present invention is preferably used for plants such as cereals; vegetables; root vegetables; tubers and roots; flowers and ornamental plants; fruit trees; ornamental foliage plants and trees of tea, coffee, cacao, and the like; feed crops; lawn grasses; and cotton.

In the application to plants, the pest control agent or the insecticide or acaricide of the present invention may be used for any site such as a leaf, a stem, a stalk, a flower, a bud, a fruit, a seed, a sprout, a root, a tuber, a tuberous root, a shoot, or a slip.

The pest control agent or the insecticide or acaricide of the present invention is not particularly limited by the species of the plant to which the pest control agent or the insecticide or acaricide is applied. As the plant species, for example, an original species, a variant species, an improved variety, a cultivar, a mutant, a hybrid, a genetically modified organism (GMO) or the like may be exemplified.

The pest control agent of the present invention may be used in seed treatment, foliage application, soil application, submerged application, or the like in order to control various agricultural insect pests and mites.

Specific examples of various agricultural insect pests and mites controllable with the pest control agent of the present invention will be shown below.

-   (1) Butterflies or moths of the order Lepidoptera -   (a) moths of the family Arctiidae, for example, Hyphantria cunea and     Lemyra imparilis; -   (b) moths of the family Bucculatricidae, for example, Bucculatrix     pyrivorella; -   (c) moths of the family Carposinidae, for example, Carposina     sasakii; -   (d) moths of the family Crambidae, for example, Diaphania indica and     Diaphania nitidalis of Diaphania spp.; for example, Ostrinia     furnacalis, Ostrinia nubilalis, and Ostrinia scapulalis of Ostrinia     spp.; and Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes     punctiferalis, Diatraea grandiosella, Glyphodes pyloalis, Hellula     undalis, and Parapediasia teterrella; -   (e) moths of the family Gelechiidae, for example, Helcystogramma     triannulella, Pectinophora gossypiella, Phthorimaea operculella, and     Sitotroga cerealella; -   (f) moths of the family Geometridae, for example, Ascotis selenaria; -   (g) moths of the family Gracillariidae, for example, Caloptilia     theivora, Phyllocnistis citrella, and Phyllonorycter ringoniella; -   (h) butterflies of the family Hesperiidae, for example, Parnara     guttata;

(i) moths of the family Lasiocampidae, for example, Malacosoma neustria;

(j) moths of the family Lymantriidae, for example, Lymantria dispar and Lymantria monacha of Lymantria spp.; and Euproctis pseudoconspersa and Orgyia thyellina;

-   (k) moths of the family Lyonetiidae, for example, Lyonetia clerkella     and Lyonetia prunifoliella malinella of Lyonetia spp.; -   (1) moths of the family Noctuidae, for example, Spodoptera     depravata, Spodoptera eridania, Spodoptera exigua, Spodoptera     frugiperda, Spodoptera littoralis, and Spodoptera litura of     Spodoptera spp.; for example, Autographa gamma and Autographa     nigrisigna of Autographa spp.; for example, Agrotis ipsilon and     Agrotis segetum of Agrotis spp.; for example, Helicoverpa armigera,     Helicoverpa assulta, and Helicoverpa zea of Helicoverpa spp.; for     example, Heliothis armigera and Heliothis virescens of Heliothis     spp.; and Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus,     Mamestra brassicae, Mythimna separata, Naranga aenescens, Panolis     japonica, Peridroma saucia, Pseudoplusia includens, and Trichoplusia     ni; -   (m) moths of the family Nolidae, for example, Earias insulana; -   (n) butterflies of the family Pieridae, for example, Pieris     brassicae and Pieris rapae crucivora of Pieris spp.; -   (o) moths of the family Plutellidae, for example, Acrolepiopsis     sapporensis and Acrolepiopsis suzukiella of Acrolepiopsis spp.; and     Plutella xylostella; -   (p) moths of the family Pyralidae, for example, Cadra cautella,     Elasmopalpus lignosellus, Etiella zinckenella, and Galleria     mellonella;

(q) moths of the family Sphingidae, for example, Manduca quinquemaculata and Manduca sexta of Manduca spp.;

-   (r) moths of the family Stathmopodidae, for example, Stathmopoda     masinissa; -   (s) moths of the family Tineidae, for example, Tinea translucens; -   (t) moths of the family Tortricidae, for example, Adoxophyes honmai     and Adoxophyes orana of Adoxophyes spp.; for example, Archips     breviplicanus and Archips fuscocupreanus of Archips spp.; and     Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella,     Grapholitha molesta, Homona magnanima, Leguminivora glycinivorella,     Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, and     Sparganothis pilleriana;

(u) moths of the family Yponomeutidae, for example, Argyresthia conjugella.

-   (2) Insect pests of the order Thysanoptera -   (a) insect pests of the family Phlaeothripidae, for example,     Ponticulothrips diospyrosi; -   (b) insect pests of the family Thripidae, for example, Frankliniella     intonsa and Frankliniella occidentalis of Frankliniella spp.; for     example, Thrips palmi and Thrips tabaci of Thrips spp.; and     Heliothrips haemorrhoidalis and Scirtothrips dorsalis. -   (3) Insect pests of the order Hemiptera -   (A) the suborder Archaeorrhyncha -   (a) insect pests of the family Delphacidae, for example, Laodelphax     striatella, Nilaparvata lugens, Perkinsiella saccharicida, and     Sogatella furcifera. -   (B) the suborder Clypeorrhyncha -   (a) insect pests of the family Cicadellidae, for example, Empoasca     fabae, Empoasca nipponica, Empoasca onukii, and Empoasca sakaii of     Empoasca spp.; and Arboridia apicalis, Balclutha saltuella,     Epiacanthus stramineus, Macrosteles striifrons, and Nephotettix     cinctinceps. -   (C) the suborder Heteroptera -   (a) insect pests of the family Alydidae, for example, Riptortus     clavatus; -   (b) insect pests of the family Coreidae, for example, Cletus     punctiger and Leptocorisa chinensis; -   (c) insect pests of the family Lygaeidae, for example, Blissus     leucopterus, Cavelerius saccharivorus, and Togo hemipterus; -   (d) insect pests of the family Miridae, for example, Halticus     insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema     sibiricum, Stenotus rubrovittatus, and Trigonotylus caelestialium; -   (e) insect pests of the family Pentatomidae, for example, Nezara     antennata and Nezara viridula of Nezara spp.; for example,     Eysarcoris aeneus, Eysarcoris lewisi, and Eysarcoris ventralis of     Eysarcoris spp.; and Dolycoris baccarum, Eurydema rugosum, Glaucias     subpunctatus, Halyomorpha halys, Piezodorus hybneri, Plautia     crossota, and Scotinophora lurida; -   (f) insect pests of the family Pyrrhocoridae, for example, Dysdercus     cingulatus; -   (g) insect pests of the family Rhopalidae, for example, Rhopalus     msculatus; -   (h) insect pests of the family Scutelleridae, for example,     Eurygaster integriceps; -   (i) insect pests of the family Tingidae, for example, Stephanitis     nashi. -   (D) the suborder Sternorrhyncha -   (a) insect pests of the family Adelgidae, for example, Adelges     laricis; -   (b) insect pests of the family Aleyrodidae, for example, Bemisia     argentifolii and Bemisia tabaci of Bemisia spp.; and Aleurocanthus     spiniferus, Dialeurodes citri, and Trialeurodes vaporariorum; -   (c) insect pests of the family Aphididae, for example, Aphis     craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis pomi,     Aphis sambuci, and Aphis spiraecola of Aphis spp.; for example,     Rhopalosiphum maidis and Rhopalosiphum padi of Rhopalosiphum spp.;     for example, Dysaphis plantaginea and Dysaphis radicola of Dysaphis     spp.; for example, Macrosiphum avenae and Macrosiphum euphorbiae of     Macrosiphum spp.; for example, Myzus cerasi, Myzus persicae, and     Myzus varians of Myzus spp.; and Acyrthosiphon pisum, Aulacorthum     solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon     fragaefolii, Hyalopterus pruni, Hyperomyzus lactucae, Lipaphis     erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia     ribis-nigri, Phorodon humuli, Schizaphis graminum, Sitobion avenae,     and Toxoptera aurantii; -   (d) insect pests of the family Coccidae, for example, Ceroplastes     ceriferus and Ceroplastes rubens of Ceroplastes spp.; -   (e) insect pests of the family Diaspididae, Pseudaulacaspis     pentagona and Pseudaulacaspis prunicola of Pseudaulacaspis spp.; for     example, Unaspis euonymi and Unaspis yanonensis of Unaspis spp.; and     Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, and     Pseudaonidia paeoniae; -   (f) insect pests of the family Margarodidae, for example, Drosicha     corpulenta and Icerya purchasi; -   (g) insect pests of the family Phylloxeridae, for example, Viteus     vitifolii; -   (h) insect pests of the family Pseudococcidae, for example,     Planococcus citri and Planococcus kuraunhiae of Planococcus spp.;     and Phenacoccus solani and Pseudococcus comstocki; -   (i) insect pests of the family Psyllidae, for example, Psylla mali     and Psylla pyrisuga of Psylla spp.; and Diaphorina citri. -   (4) Insect pests of the suborder Polyphaga -   (a) insect pests of the family Anobiidae, for example, Lasioderma     serricorne; -   (b) insect pests of the family Attelabidae, for example, Byctiscus     betulae and Rhynchites heros; -   (c) insect pests of the family Bostrichidae, for example, Lyctus     brunneus; -   (d) insect pests of the family Brentidae, for example, Cylas     formicarius; -   (e) insect pests of the family Buprestidae, for example, Agrilus     sinuatus; -   (f) insect pests of the family Cerambycidae, for example,     Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and     Xylotrechus pyrrhoderus; -   (g) insect pests of the family Chrysomelidae, for example, Bruchus     pisorum and Bruchus rufimanus of Bruchus spp.; for example,     Diabrotica barberi, Diabrotica undecimpunctata, and Diabrotica     virgifera of Diabrotica spp.; for example, Phyllotreta nemorum and     Phyllotreta striolata of Phyllotreta spp.; and Aulacophora     femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema     concinna, Leptinotarsa decemlineata, Oulema oryzae, and Psylliodes     angusticollis; -   (h) insect pests of the family Coccinellidae, for example, Epilachna     varivestis and Epilachna vigintioctopunctata of Epilachna spp.; -   (i) insect pests of the family Curculionidae, for example,     Anthonomus grandis and Anthonomus pomorum of Anthonomus spp.; for     example, Sitophilus granarius and Sitophilus zeamais of Sitophilus     spp.; and Echinocnemus squameus, Euscepes postfasciatus, Hylobius     abietis, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus     sulcatus, Sitona lineatus, and Sphenophorus venatus; -   (j) insect pests of the family Elateridae, for example, Melanotus     fortnumi and Melanotus tamsuyensis of Melanotus spp.; -   (k) insect pests of the family Nitidulidae, for example, Epuraea     domina; -   (1) insect pests of the family Scarabaeidae, for example, Anomala     cuprea and Anomala rufocuprea of Anomala spp.; and Cetonia aurata,     Gametis jucunda, Heptophylla picea, Melolontha melolontha, and     Popillia japonica; -   (m) insect pests of the family Scolytidae, for example, Ips     typographus; -   (n) insect pests of the family Staphylinidae, for example, Paederus     fuscipes; -   (o) insect pests of the family Tenebrionidae, for example, Tenebrio     molitor and Tribolium castaneum; -   (p) insect pests of the family Trogossitidae, for example,     Tenebroides mauritanicus. -   (5) Insect pests of the order Diptera

(A) the suborder Brachycera

(a) insect pests of the family Agromyzidae, for example, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, and Liriomyza trifolii of Liriomyza spp.; and Chromatomyia horticola and Agromyza oryzae;

-   (b) insect pests of the family Anthomyiidae, for example, Delia     platura and Delia radicum of Delia spp.; and Pegomya cunicularia; -   (c) insect pests of the family Drosophilidae, for example,     Drosophila melanogaster and Drosophila suzukii of Drosophila spp.; -   (d) insect pests of the family Ephydridae, for example, Hydrellia     griseola; -   (e) insect pests of the family Psilidae, for example, Psila rosae; -   (f) insect pests of the family Tephritidae, for example, Bactrocera     cucurbitae and Bactrocera dorsalis of Bactrocera spp.; for example,     Rhagoletis cerasi and Rhagoletis pomonella of Rhagoletis spp.; and     Ceratitis capitata and Dacus oleae. -   (B) the suborder Nematocera -   (a) insect pests of the family Cecidomyiidae, for example,     Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor,     and Sitodiplosis mosellana. -   (6) Insect pests of the order Orthoptera -   (a) insect pests of the family Acrididae, for example, Schistocerca     americana and Schistocerca gregaria of Schistocerca spp.; and     Chortoicetes terminifera, Dociostaurus maroccanus, Locusta     migratoria, Locustana pardalina, Nomadacris septemfasciata, and Oxya     yezoensis; -   (b) insect pests of the family Gryllidae, for example, Acheta     domestica and Teleogryllus emma; -   (c) insect pests of the family Gryllotalpidae, for example,     Gryllotalpa orientalis;

(d) insect pests of the family Tettigoniidae, for example, Tachycines asynamorus.

-   (7) Acari -   (A) Acaridida of the order Astigmata -   (a) mites of the family Acaridae, for example, Rhizoglyphus     echinopus and Rhizoglyphus robini of Rhizoglyphus spp.; for example,     Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus     putrescentiae, and Tyrophagus similis of Tyrophagus spp.; and Acarus     siro, Aleuroglyphus ovatus, and Mycetoglyphus fungivorus; -   (B) Actinedida of the order Prostigmata -   (a) mites of the family Tetranychidae, for example, Bryobia     praetiosa and Bryobia rubrioculus of Bryobia 6 spp.; for example,     Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis,     Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus     pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus     suginamensis, and Eotetranychus uncatus of Eotetranychus spp.; for     example, Oligonychus hondoensis, Oligonychus ilicis, Oligonychus     karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus     perseae, Oligonychus pustulosus, Oligonychus shinkajii, and     Oligonychus ununguis of Oligonychus spp.; for example, Panonychus     citri, Panonychus mori, and Panonychus ulmi of Panonychus spp.; for     example, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus     ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus     urticae, Tetranychus viennensis, and Tetranychus evansi of     Tetranychus spp.; for example, Aponychus corpuzae and Aponychus     firmianae of Aponychus spp.; for example, Sasanychus akitanus and     Sasanychus pusillus of Sasanychus spp.; for example,     Schizotetranychus celarius, Schizotetranychus longus,     Schizotetranychus miscanthi, Schizotetranychus recki, and     Schizotetranychus schizopus of Schizotetranychus spp.; and     Tetranychina harti, Tuckerella pavoniformis, and Yezonychus     sapporensis;

-   (b) mites of the family Tenuipalpidae, for example, Brevipalpus     lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus     russulus, and Brevipalpus californicus of Brevipalpus spp.; for     example, Tenuipalpus pacificus and Tenuipalpus zhizhilashviliae of     Tenuipalpus spp.; and Dolichotetranychus floridanus; -   (c) mites of the family Eriophyidae, for example, Aceria diospyri,     Aceria ficus, Aceria japonica, Aceria kuko, Aceria paradianthi,     Aceria tiyingi, Aceria tulipae,and Aceria zoysiea of Aceria spp.;     for example, Eriophyes chibaensis and Eriophyes emarginatae of     Eriophyes spp.; for example, Aculops lycopersici and Aculops     pelekassi of Aculops spp.; for example, Aculus fockeui and Aculus     schlechtendali of Aculus spp.; and Acaphylla theavagrans, Calacarus     carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri,     Paraphytoptus kikus, Paracalacarus podocarpi, and Phyllocotruta     citri; -   (d) mites of the family Tarsonemidae, for example, Tarsonemus     bilobatus and Tarsonemus waitei of Tarsonemus spp.; and Phytonemus     pallidus and Polyphagotarsonemus latus; -   (e) mites of the family Penthaleidae, for example, Penthaleus     erythrocephalus and Penthaleus major of Penthaleus spp.

The pest control agent of the present invention may be used as a mixture or in combination with another active ingredient such as a fungicide, an insecticide or acaricide, a nematicide, or a pesticide for soil insect pests; a plant regulating agent, a synergist, a fertilizer, a soil improvement agent, animal feed, or the like.

The combination of the heteroaryl azole compound of the present invention with another active ingredient may be expected to have synergistic effects on insecticidal, miticidal, or nematicidal activity. The synergistic effects may be confirmed by the equation of Colby (Colby. S. R.; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, p. 20-22, 1967) according to a standard method.

Specific examples of the insecticide or acaricide, the nematicide, the pesticide for soil insect pests, the anthelmintic agent, and the like that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.

-   (1) Acetylcholinesterase inhibitors:     -   (a) carbamate-based: alanycarb, aldicarb, bendiocarb,         benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,         carbosulfan, ethiofencarb, fenobucarb, formetanate,         furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl,         pirimicarb, propoxur, thiodicarb, thiofanox, triazamate,         trimethacarb, XMC, xylylcarb, fenothiocarb, MIPC, MPMC, MTMC,         aldoxycarb, allyxycarb, aminocarb, bufencarb, cloethocarb, metam         sodium, and promecarb;     -   (b) organophosphorus-based: acephate, azamethiphos,         azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos,         chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,         coumaphos, cyanophos, demeton-S-methyl, diazinon,         dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos,         disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos,         fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,         isofenphos, isocarbophos, isoxathion, malathion, mecarbam,         methamidophos, methidathion, mevinphos, monocrotophos, naled,         omethoate, oxydemeton-methyl, parathion, parathion-methyl,         phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,         pirimiphos-methyl, profenofos, propetamphos, prothiofos,         pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos,         temephos, terbufos, tetrachlorvinphos, thiometon, triazophos,         trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion,         cyanofenphos, CYAP, demeton-S-methyl sulfone, dialifos,         dichlofenthion, dioxabenzofos, etrimfos, fensulfothion,         flupyrazofos, fonofos, formothion, fosmethilan, isazofos,         iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb,         propaphos, prothoate, and sulprofos. -   (2) GABAergic chloride ion channel antagonists: acetoprole,     chlordene, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole,     camphechlor, heptachlor, and dienochlor. -   (3) Sodium channel modulators: acrinathrin, d-cis-trans allethrin,     d-trans allethrin, bifenthrin, bioallethrin, bioallethrin     s-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,     β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin,     cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin,     ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin,     empenthrin [(EZ)-(1R)-Isomer], esfenvalerate, etofenprox,     fenpropathrin, fenvalerate, flucythrinate, flumethrin,     τ-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin,     phenothrin [(1R)-trans isomer], prallethrin, pyrethrum, resmethrin,     silafluofen, tefluthrin, tetramethrin [(1R)-isomer], tralomethrin,     transfluthrin, allethrin, pyrethrins, pyrethrin I, pyrethrin II,     profluthrin, dimefluthrin, bioethanomethrin, biopermethrin,     transpermethrin, fenfluthrin, fenpirithrin, flubrocythrinate,     flufenprox, metofluthrin, protrifenbute, pyresmethrin, and     terallethrin. -   (4) Nicotinic acetylcholine receptor agonists: acetamiprid,     clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine,     thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone,     and flupyrimine. -   (5) Nicotinic acetylcholine receptor allosteric modulators:     spinetoram and spinosad. -   (6) Chloride channel activators: abamectin, emamectin-benzoate,     lepimectin, milbemectin, ivermectin, selamectin, doramectin,     eprinomectin, moxidectin, milbemycin, milbemycin oxime, and     nemadectin. -   (7) Juvenile hormone-like substances: hydroprene, kinoprene,     methoprene, fenoxycarb, pyriproxyfen, diofenolan, epofenonane, and     triprene. -   (8) Other nonspecific inhibitors: methyl bromide, chloropicrin,     sulfuryl fluoride, borax, and tartar emetic. -   (9) Homoptera selective feeding inhibitors: flonicamid, pymetrozine,     and pyrifluquinazon. -   (10) Mite growth inhibitors: clofentezine, diflovidazin,     hexythiazox, and etoxazole. -   (11) Insect midgut inner membrane disrupting agents derived from     microorganisms: Bacillus thuringiensis subsp. Israelensis, Bacillus     sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus     thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp.     tenebrionis, and Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa,     Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, and     Cry34Ab1/Cry35Ab1. -   (12) Mitochondrial ATP biosynthetic enzyme inhibitors:     diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite,     and tetradifon. -   (13) Oxidative phosphorylation uncouplers: chlorfenapyr,     sulfluramid, DNOC, binapacryl, dinobuton, and dinocap. -   (14) Nicotinic acetylcholine receptor channel blockers: bensultap,     cartap hydrochloride, nereistoxin, thiosultap-sodium, and     thiocyclam. -   (15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron,     diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron,     novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, and     fluazuron. -   (16) Diptera molting disrupting agents: cyromazine. -   (17) Molting hormone receptor agonists: chromafenozide,     halofenozide, methoxyfenozide, and tebufenozide. -   (18) Octopamine receptor agonists: amitraz, demiditraz, and     chlordimeform. -   (19) Mitochondrial electron transport system complex III inhibitors:     acequinocyl, fluacrypyrim, and hydramethylnon. -   (20) Mitochondrial electron transport system complex I inhibitors:     fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad,     tolfenpyrad, and rotenone. -   (21) Voltage-gated sodium channel blockers: indoxacarb and     metaflumizone. -   (22) Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen,     and spirotetramat. -   (23) Mitochondrial electron transport system complex IV inhibitors:     aluminum phosphide, calcium phosphide, phosphine, zinc phosphide,     and cyanide. -   (24) Mitochondrial electron transport system complex II inhibitors:     cyenopyrafen, cyflumetofen, and pyflubumide. -   (25) Ryanodine receptor modulators: chlorantraniliprole,     cyantraniliprole, flubendiamide, cyclaniliprole, and tetraniliprole. -   (26) Mixed function oxidase inhibitor compounds: piperonyl butoxide. -   (27) Latrophilin receptor agonists: depsipeptide, cyclodepsipeptide,     24 membered cyclodepsipeptide, and emodepside. -   (28) Other agents (based on an unknown mechanism of action):     azadirachtin, benzoximate, bifenazate, bromopropylate,     quinomethionate, cryolite, dicofol, pyridalyl, benclothiaz, sulfur,     amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate,     metaldehyde, chlorobenzilate, clothiazoben, dicyclanil, fenoxacrim,     fentrifanil, flubenzimine, fluphenazine, gossyplure, japonilure,     metoxadiazone, oil, potassium oleate, tetrasul, triarathene,     afidopyropen, flometoquin, flufiprole, fluensulfone, meperfluthrin,     tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide,     fluralaner, afoxolaner, fluxametamide,     5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitrile     (CAS: 943137-49-3), broflanilide, other m-diamides, steinernema     carpocapsae, steinernema glaseri, pasteuria penetrans, paecilomyces     tenuipes, paecilomyces fumosoroseus, beauveria bassiana, beauveria     brongniartii, metarhizium anisopliae, verticillium lecanii,     acynonapyr benzpyrimoxan, oxazosulfyl, tyclopyrazoflor, and     fluhexafon. -   (29) Anthelmintic agents: -   (a) benzimidazole-based: fenbendazole, albendazole, triclabendazole,     oxibendazole, mebendazole, oxfendazole, parbendazole, flubendazole,     febantel, netobimin, thiophanate, thiabendazole, and cambendazole; -   (b) salicylanilide-based: closantel, oxyclozanide, rafoxanide, and     niclosamide; -   (c) substituted phenol-based: nitroxinil and nitroscanate; -   (d) pyrimidine-based: pyrantel and morantel; -   (e) imidazothiazole-based: levamisole and tetramisole; -   (f) tetrahydropyrimidine-based: praziquantel and epsiprantel; -   (g) other anthelmintic agents: cyclodiene, ryania, clorsulon,     metronidazole, demiditraz, piperazine, diethylcarbamazine,     dichlorophen, monepantel, tribendimidine, amidantel,     thiacetarsamide, melarsomine, and arsenamide.

Specific examples of the fungicide that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.

-   (1) Nucleic acid biosynthesis inhibitors:     -   (a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M,         furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, and         ofurace;     -   (b) adenosine deaminase inhibitors: bupirimate, dimethirimol,         and ethirimol;     -   (c) DNA/RNA synthesis inhibitors: hymexazol and octhilinone;     -   (d) DNA topoisomerase II inhibitors: oxolinic acid. -   (2) Mitotic inhibitors and cell division inhibitors:     -   (a) β-tubulin polymerization inhibitors: benomyl, carbendazim,         chlorfenazole, fuberidazole, thiabendazole, thiophanate,         thiophanate-methyl, diethofencarb, zoxamide, and ethaboxam;     -   (b) cell division inhibitors: pencycuron;     -   (c) spectrin-like protein delocalization inhibitors:         fluopicolide. -   (3) Respiration inhibitors:     -   (a) complex I NADH oxidation-reduction enzyme inhibitors:         diflumetorim and tolfenpyrad;     -   (b) complex II succinate dehydrogenase inhibitors: benodanil,         flutolanil, mepronil, isofetamid, fluopyram, fenfuram,         furmecyclox, carboxin, oxycarboxin, thifluzamide,         benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam,         penflufen, penthiopyrad, sedaxane, boscalid, pyraziflumid,         pydiflumetofen, isoflucypram, and inpyrfluxam;     -   (c) complex III ubiquinol oxidase Qo inhibitors: azoxystrobin,         coumoxystrobin, coumethoxystrobin, enoxastrobin,         flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin,         pyrametostrobin, triclopyricarb, kresoxim-methyl,         trifloxystrobin, dimoxystrobin, fenaminstrobin, metominostrobin,         orysastrobin, famoxadone, fluoxastrobin, fenamidone,         pyribencarb, mandestrobin and metyltetraprole;     -   (d) complex III ubiquinol reductase Qi inhibitors: cyazofamid,         amisulbrom, and fenpicoxamid;     -   (e) oxidative phosphorylation uncoupling agents: binapacryl,         meptyldinocap, dinocap, fluazinam, and ferimzone;     -   (f) oxidative phosphorylation inhibitors (ATP synthase         inhibitors): fentin acetate, fentin chloride, and fentin         hydroxide;     -   (g) ATP production inhibitors: silthiofam;     -   (h) complex III: Qx (unknown) inhibitor of cytochrome bcl         (ubiquinone reductase): ametoctradin. -   (4) Amino acid and protein synthesis inhibitors     -   (a) methionine biosynthesis inhibitors: andoprim, cyprodinil,         mepanipyrim, and pyrimethanil;     -   (b) protein synthesis inhibitors: blasticidin-S, kasugamycin,         kasugamycin hydrochloride, streptomycin, and oxytetracycline. -   (5) Signal transduction inhibitors:     -   (a) signal transduction inhibitors: quinoxyfen and proquinazid;     -   (b) MAP/histidine kinase inhibitors in osmotic signal         transduction: fenpiclonil, fludioxonil, chlozolinate, iprodione,         procymidone, and vinclozolin. -   (6) Lipid and cell membrane synthesis inhibitors:     -   (a) phospholipid biosynthesis, methyltransferase inhibitors:         edifenphos, iprobenfos, pyrazophos, and isoprothiolane;     -   (b) lipid peroxidation agents: biphenyl, chloroneb, dichloran,         quintozene, tecnazene, tolclofos-methyl, and etridiazole;     -   (c) agents that act on cell membranes: iodocarb, propamocarb,         propamocarb-hydrochloride, propamocarb-fosetylate, and         prothiocarb;     -   (d) microorganisms that disrupt cell membranes of pathogens:         Bacillus subtilis, Bacillus subtilis strain QST713 strain,         Bacillus subtilis FZB24, Bacillus subtilis strain MBI600,         Bacillus subtilis strain D747, and Bacillus amyloliquefaciens;     -   (e) agents that disrupt cell membranes: Melaleuca alternifolia         (tea tree) extract. -   (7) Cell membrane sterol biosynthesis inhibitors:     -   (a) C14-demethylation inhibitors in sterol biosynthesis:         triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol,         nuarimol, imazalil, imazalil-sulfate, oxpoconazole fumarate,         pefurazoate, prochloraz, triflumizole, viniconazole,         azaconazole, bitertanol, bromuconazole, cyproconazole,         diclobutrazol, difenoconazole, diniconazole, diniconazole-M,         epoxiconazole, etaconazole, fenbuconazole, fluquinconazole,         flusilazole, flutriafol, furconazole, furconazole-cis,         hexaconazole, imibenconazole, ipconazole, metconazole,         myclobutanil, penconazole, propiconazole, fluquinconazole,         simeconazole, tebuconazole, tetraconazole, triadimefon,         triadimenol, triticonazole, prothioconazole, voriconazole and         mefentrifluconazole;     -   (b) Δ14 reductase and sterol Δ8→Δ7-isomerase inhibitors in         sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate,         fenpropimorph, tridemorph, fenpropidin, piperalin, and         spiroxamine;     -   (c) 3-keto reductase inhibitors in C4-demethylation in the         sterol biosynthesis system: fenhexamid and fenpyrazamine;     -   (d) squalene epoxidase inhibitors in the sterol biosynthesis         system: pyributicarb, naftifine, and terbinafine. -   (8) Cell wall synthesis inhibitors     -   (a) trehalase inhibitors: validamycin;     -   (b) chitin synthase inhibitors: polyoxins and polyoxorim;     -   (c) cellulose synthase inhibitors: dimethomorph, flumorph,         pyrimorph, benthiavalicarb-isopropyl, iprovalicarb,         valifenalate, and mandipropamid. -   (9) Melanin biosynthesis inhibitors     -   (a) melanin biosynthesis reductase inhibitors: fthalide,         pyroquilon, and tricyclazole;     -   (b) melanin biosynthesis anhydrase inhibitors: carpropamid,         diclocymet, and fenoxanil;     -   (c) melanin biosynthesis polyketide synthesis inhibitors:         tolprocarb. -   (10) Host plant resistance inducers:     -   (a) agents that act on salicylic acid synthesis pathway:         acibenzolar-S-methyl;     -   (b) others: probenazole, tiadinil, isotianil, dichlobentiazox,         laminarin, and reynoutria sachalinensis extract. -   (11) Agents with unknown mode of action: cymoxanil,     fosetyl-aluminum, phosphoric acid (phosphate), tecloftalam,     triazoxide, flusulfamide, diclomezine, methasulfocarb, cyflufenamid,     metrafenone, pyriofenone, dodine, dodine free base, and flutianil. -   (12) Agents having multiple active sites: copper (copper salt),     bordeaux mixture, copper hydroxide, copper naphthalate, copper     oxide, copper oxychloride, copper sulfate, sulfur, sulfur products,     calcium polysulfide, ferbam, mancozeb, maneb, mancopper, metiram,     polycarbamate, propineb, thiram, zineb, ziram, captan, captafol,     folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine,     iminoctadine triacetate, iminoctadine trialbesilate, anilazine,     dithianon, quinomethionate, and fluoroimide.     -   (13) Other agents: DBEDC, fluorofolpet, guazatine acetate,         bis(8-quinolinolato)copper(II), propamidine, chloropicrin,         cyprofuram, agrobacterium, bethoxazin, diphenylamine, methyl         isothiocyanate (MITC), mildiomycin, capsaicin, cufraneb,         cyprosulfamide, dazomet, debacarb, dichlorophen, flumetover,         fosetyl-calcium, fosetyl-sodium, irumamycin, natamycin,         nitrothal isopropyl, oxamocarb, pyrrolnitrin, tebufloquin,         tolnifanide, zarilamide, algophase, amicarthiazol,         oxathiapiprolin, metiram zinc, benthiazole, trichlamide,         uniconazole, oxyfenthiin, picarbutrazox, dichlobentiazox,         quinofumelin, thiuram, ambam, Agrobacterium radiobacter,         Coniothyrium minitans, Pseudomonas fluorescens, Pseudomonas         rhodesiae, Talaromyces flavus, Trichoderma atroviride, Erwinia         carotovora subsp. carotovora, Bacillus simplex, Variovorax         paradoxus, Lactobacillus plantarum, florylpicoxamid,         pyrapropoyne, fluindapyr, aminopyrifen, pyridachlometyl, and         ipflufenoquin.

Specific examples of the plant regulating agent that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.

Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl aminoethoxyvinyl glycine (also called aviglycine), aminooxyacetate, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyrate, dichlorprop, phenothiol, 1-naphthyl acetamide, ethychlozate, cloxyfonac, maleic acid hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (−)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-amino levulinic acid, and daminozide.

[Ectoparasite Control Agent]

The ectoparasite control agent of the present invention contains at least one active ingredient selected from the heteroaryl azole compounds of the present invention. The amount of the heteroaryl azole compound contained in the ectoparasite control agent of the present invention is not particularly limited as long as its ectoparasite control effect is exhibited.

As the host animal to be treated with the ectoparasite control agent of the present invention, a warm-blooded animal such as a human and a livestock mammal (e.g., a cow, a horse, a pig, sheep, and a goat), a laboratory animal (e.g., a mouse, a rat, and a sand rat), a pet animal (e.g., a hamster, a guinea pig, a dog, a cat, a squirrel, a rabbit, and a ferret), wild and zoo mammals (e.g., a monkey, a fox, a deer, and a buffalo), a fowl (e.g., a turkey, a duck, a chicken, a quail, and a goose), and a pet bird (e.g., a pigeon, a parrot, a myna bird, a Java sparrow, a parakeet, a Bengalese finch, and a canary bird); and fishes such as salmon, trout, and koi may be exemplified. In addition, a bee, a stag beetle and a beetle may be exemplified.

The ectoparasite control agent of the present invention may be applied by a known veterinary approach (local, oral, parenteral or subcutaneous administration). As the method therefor, a method of orally administering tablets, capsules, feed or the like containing the ectoparasite control agent to animals; a method of administering the ectoparasite control agent through dipping liquids, suppositories, injection (intramuscular, subcutaneous, intravenous, or intraperitoneal injection, etc.) or the like to animals; a method of locally administering oily or aqueous liquid formulations by spraying, pour-on, spot-on or the like; and a method of kneading the ectoparasite control agent into a resin, shaping the kneaded product into a suitable shape such as a collar or an ear tag, and attaching it to animals for local administration; or the like may be exemplified.

Ectoparasites parasitize the inside or the body surface of host animals, particularly, warm-blooded animals. Specifically, the ectoparasites parasitize the backs, armpits, lower abdomens, inner thighs, or the like of host animals and live by obtaining nutrients such as blood or dandruff from the animals. As the ectoparasite, mites, lice, fleas, a mosquito, a stable fly, a flesh fly or the like may be exemplified. Specific examples of the ectoparasite controllable with the ectoparasite control agent of the present invention will be shown below.

-   (1) Acari -   mites of the family Dermanyssidae, mites of the family     Macronyssidae, mites of the family Laelapidae, mites of the family     Varroidae, mites of the family Argasidae, mites of the family     Ixodidae, mites of the family Psoroptidae, mites of the family     Sarcoptidae, mites of the family Knemidokoptidae, mites of the     family Demodixidae, mites of the family Trombiculidae, and insect     parasitic mites such as mites of the family Canestriniidae. -   (2) The order Phthiraptera -   lice of the family Haematopinidae, lice of the family Linognathidae,     bird lice of the family Menoponidae, bird lice of the family     Philopteridae, and bird lice of the family Trichodectidae. -   (3) The order Siphonaptera -   fleas of the family Pulicidae, for example, Ctenocephalides canis     and Ctenocephalides felis of Ctenocephalides spp.; -   fleas of the family Tungidae, fleas of the family Ceratophyllidae,     and fleas of the family Leptopsyllidae. -   (4) The order Hemiptera -   (5) Insect pests of the order Diptera mosquitos of the family     Culicidae, black flies of the family Simuliidae, biting midges of     the family Ceratopogonidae, horseflies of the family Tabanidae,     flies of the family Muscidae, tsetse flies of the family     Glossinidae, flesh flies of the family Sarcophagidae, flies of the     family Hippoboscidae, flies of the family Calliphoridae, and flies     of the family Oestridae. -   [Endoparasite Control Agent or Expellant]

The endoparasite control agent or expellant of the present invention contains at least one active ingredient selected from the heteroaryl azole compounds of the present invention. The amount of the heteroaryl azole compound contained in the endoparasite control agent or expellant of the present invention is not particularly limited as long as its endoparasite control effect is exhibited.

The parasite targeted by the endoparasite control agent or expellant of the present invention parasitizes the inside of host animals, particularly, warm-blooded animals or fishes (endoparasite). As the host animal for which the endoparasite control agent or expellant of the present invention is effective, a warm-blooded animal such as a human and a livestock mammal (e.g., a cow, a horse, a pig, sheep, and a goat), a laboratory animal (e.g., a mouse, a rat, and a sand rat), a pet animal (e.g., a hamster, a guinea pig, a dog, a cat, a squirrel, a rabbit, and a ferret), wild and zoo mammals (e.g., a monkey, a fox, a deer, and a buffalo), a fowl (e.g., a turkey, a duck, a chicken, a quail, and a goose), and a pet bird (e.g., a pigeon, a parrot, a myna bird, a Java sparrow, a parakeet, a Bengalese finch, and a canary bird); and fishes such as salmon, trout, and koi may be exemplified. Parasitic diseases mediated by parasites may be prevented or treated by controlling and expelling the parasites.

As the parasite to be controlled or expelled, the following may be exemplified.

-   (1) Nematodes of the order Dioctophymatida -   (a) kidney worms of the family Dioctophymatidae, for example,     Dioctophyma renale of Dioctophyma spp.; -   (b) kidney worms of the family Soboliphymatidae, for example,     Soboliphyme abei and Soboliphyme baturini of Soboliphyme spp. -   (2) Nematodes of the order Trichocephalida -   (a) trichinae of the family Trichinellidae, for example, Trichinella     spiralis of Trichinella spp.; -   (b) whipworms of the family Trichuridae, for example, Capillaria     annul ata, Capillaria contorta, Capillaria hepatica, Capillaria     perforans, Capillaria plica, and Capillaria suis of Capillaria spp.;     and Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris     skrjabini, and Trichuris suis of Trichuris spp. -   (3) Nematodes of the order Rhabditida -   threadworms of the family Strongyloididae, for example,     Strongyloides papillosus, Strongyloides planiceps, Strongyloides     ransomi, Strongyloides suis, Strongyloides stercoralis,     Strongyloides tumefaciens, and Strongyloides ratti of Strongyloides     spp. -   (4) Nematodes of the order Strongylida hookworms of the family     Ancylostomatidae, for example, Ancylostoma braziliense, Ancylostoma     caninum, Ancylostoma duodenale, and Ancylostoma tubaeforme of     Ancylostoma spp.; Uncinaria stenocephala of Uncinaria spp.; and     Bunostomum phlebotomum and Bunostomum trigonocephalum of Bunostomum     spp. -   (5) Nematodes of the order Strongylida -   (a) nematodes of the family Angiostrongylidae, for example,     Aelurostrongylus abstrusus of Aelurostrongylus spp.; and     Angiostrongylus vasorum and Angiostrongylus cantonesis of     Angiostrongylus spp.; -   (b) nematodes of the family Crenosomatidae, for example, Crenosoma     aerophila and Crenosoma vulpis of Crenosoma spp.; -   (c) nematodes of the family Filaroididae, for example, Filaroides     hirthi and Filaroides osleri of Filaroides spp.; -   (d) lungworms of the family Metastrongylidae, for example,     Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus     pudendotectus, and Metastrongylus salmi of Metastrongylus spp.; -   (e) gapeworms of the family Syngamidae, for example, Cyathostoma     bronchialis of Cyathostoma spp.; and Syngamus skrjabinomorpha and     Syngamus trachea of Syngamus spp. -   (6) Nematodes of the order Strongylida -   (a) nematodes of the family Molineidae, for example, Nematodirus     filicollis and Nematodirus spathiger of Nematodirus spp.; -   (b) nematodes of the family Dictyocaulidae, for example,     Dictyocaulus filaria and Dictyocaulus viviparus of Dictyocaulus     spp.; -   (c) nematodes of the family Haemonchidae, for example, Haemonchus     contortus of Haemonchus spp.; and Mecistocirrus digitatus of     Mecistocirrus spp.; -   (d) nematodes of the family Haemonchidae, for example, Ostertagia     ostertagi of Ostertagia spp.; -   (e) nematodes of the family Heligmonellidae, for example,     Nippostrongylus braziliensis of Nippostrongylus spp.; -   (f) nematodes of the family Trichostrongylidae, for example,     Trichostrongylus axei, Trichostrongylus colubriformis, and     Trichostrongylus tennis of Trichostrongylus spp.; Hyostrongylus     rubidus of Hyostrongylus spp.; and Obeliscoides cuniculi of     Obeliscoides spp. -   (7) Nematodes of the order Strongylida -   (a) nematodes of the family Chabertiidae, for example, Chabertia     ovina of Chabertia spp.; and Oesophagostomum brevicaudatum,     Oesophagostomum columbianum, Oesophagostomum dentatum,     Oesophagostomum georgianum, Oesophagostomum maplestonei,     Oesophagostomum quadrispinulatum, Oesophagostomum radiatum,     Oesophagostomum venulosum, and Oesophagostomum watanabei of     Oesophagostomum spp.; -   (b) nematodes of the family Stephanuridae, for example, Stephanurus     dentatus of Stephanurus spp.; -   (c) nematodes of the family Strongylidae, for example, Strongylus     asini, Strongylus edentatus, Strongylus equinus, and Strongylus     vulgaris of Strongylus spp. -   (8) Nematodes of the order Oxyurida -   nematodes of the family Oxyuridae, for example, Enterobius     anthropopitheci and Enterobius vermicularis of Enterobius spp.;     Oxyuris equi of Oxyuris spp.; and Passalurus ambiguous of Passalurus     spp. -   (9) Nematodes of the order Ascaridida -   (a) nematodes of the family Ascaridiidae, for example, Ascaridia     galli of Ascaridia spp.; -   (b) nematodes of the family Heterakidae, for example, Heterakis     beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis     pusilla, and Heterakis putaustralis of Heterakis spp.;

(c) nematodes of the family Anisakidae, for example, Anisakis simplex of Anisakis spp.;

(d) nematodes of the family Ascarididae, for example, Ascaris lumbricoides and Ascaris suum of Ascaris spp.; and Parascaris equorum of Parascaris spp.;

-   (e) nematodes of the family Toxocaridae, for example, Toxocara     canis, Toxocara leonina, Toxocara suum, Toxocara vitulorum, and     Toxocara cati of Toxocara spp. -   (10) Nematodes of the order Spirurida -   (a) nematodes of the family Onchocercidae, for example, Brugia     malayi, Brugia pahangi, and Brugia patei of Brugia spp.;     Dipetalonema reconditum of Dipetalonema spp.; Dirofilaria immitis of     Dirofilaria spp.; Filaria oculi of Filaria spp.; and Onchocerca     cervicalis, Onchocerca gibsoni, and Onchocerca gutturosa of     Onchocerca spp.; -   (b) nematodes of the family Setariidae, for example, Setaria     digitata, Setaria equina, Setaria labiatopapillosa, and Setaria     marshalli of Setaria spp.; and Wuchereria bancrofti of Wuchereria     spp.; -   (c) nematodes of the family Filariidae, for example, Parafilaria     multipapillosa of Parafilaria spp.; and Stephanofilaria assamensis,     Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria     okinawaensis, and Stephanofilaria stilesi of Stephanofilaria spp. -   (11) Nematodes of the order Spirurida -   (a) nematodes of the family Gnathostomatidae, for example,     Gnathostoma doloresi and Gnathostoma spinigerum of Gnathostoma spp.; -   (b) nematodes of the family Habronematidae, for example, Habronema     majus, Habronema microstoma, and Habronema muscae of Habronema spp.;     and Draschia megastoma of Draschia spp.; -   (c) nematodes of the family Physalopteridae, for example,     Physaloptera canis, Physaloptera cesticillata, Physaloptera     erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera     papilloradiata, Physaloptera praeputialis, Physaloptera     pseudopraerutialis, Physaloptera rara, Physaloptera sibirica, and     Physaloptera vulpineus of Physaloptera spp.; -   (d) nematodes of the family Gongylonematidae, for example,     Gongylonema pulchrum of Gongylonema spp.; -   (e) nematodes of the family Spirocercidae, for example, Ascarops     strongylina of Ascarops spp.; -   (f) nematodes of the family Thelaziidae, for example, Thelazia     callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodesi,     and Thelazia skrjabini of Thelazia spp.

[Control Agent for Other Pests]

The heteroaryl azole compound of the present invention is additionally excellent in control effect on insect pests that have a stinger or venom and harm humans and animals, insect pests that mediate various pathogens or disease-causing microbes, or insect pests that cause discomfort to humans (toxic pests, hygienic pests, and obnoxious pests, etc.).

Specific examples thereof will be shown below.

-   (1) Insect pests of the order Hymenoptera bees of the family     Argidae, bees of the family Cynipidae, bees of the family     Diprionidae, ants of the family Formicidae, bees of the family     Mutillidae, and bees of the family Vespidae. -   (2) Other insect pests Blattodea, termites, Araneae, centipedes,     millipedes, crustacea, and Cimex lectularius.

[l Pharmaceutical Formulation]

Some pharmaceutical formulations of the pest control agent, the insecticide or acaricide, the ectoparasite control agent or the endoparasite control agent or expellant of the present invention will be shown. However, additives and addition ratios should not be limited by these examples and may be changed in wide ranges. The term “part” in the pharmaceutical formulations represents part by weight.

Hereinafter, the pharmaceutical formulations for agriculture or horticulture and for paddy rice will be shown.

(Preparation 1: Wettable Powder)

40 parts of the heteroaryl azole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and 3 parts of alkyl naphthalenesulfonate are uniformly mixed and finely milled to obtain a wettable powder containing 40% of the active ingredient.

(Preparation 2: Emulsion)

30 parts of the heteroaryl azole compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

(Preparation 3: Granular Formulation)

5 parts of the heteroaryl azole compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed, finely milled, and then granulated into a granular shape of 0.5 to 1.0 mm in diameter to obtain a granular formulation containing 5% of the active ingredient.

(Preparation 4: Granular Formulation)

5 parts of the heteroaryl azole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are well milled and mixed, and after addition of water, the mixture is well kneaded, then granulated, and dried to obtain a granular formulation containing 5% of the active ingredient.

(Preparation 5: Suspension)

10 parts of the heteroaryl azole compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-milled until the particle size becomes 3 microns or smaller to obtain a suspension containing 10% of the active ingredient.

Hereinafter, the pharmaceutical formulations of the ectoparasite control agent or the endoparasite control agent or expellant will be shown.

(Preparation 6: Granules)

5 parts of the heteroaryl azole compound of the present invention are dissolved in an organic solvent to obtain a solution. The solution is sprayed onto 94 parts of kaolin and 1 part of white carbon. Then, the solvent is evaporated under reduced pressure. This type of granules may be mixed with animal feed.

(Preparation 7: Injectable Filler)

0.1 to 1 part of the heteroaryl azole compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed and then sterilized by filtration through a sterilizing filter.

(Preparation 8: Pore-On Formulation)

5 parts of the heteroaryl azole compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol are uniformly mixed to obtain a pore-on formulation.

(Preparation 9: Spot-On Formulation)

10 to 15 parts of the heteroaryl azole compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on formulation.

(Preparation 10: Spray Formulation)

1 part of the heteroaryl azole compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol are uniformly mixed to obtain a spray formulation.

Next, the present invention will be more specifically described with reference to Examples of compounds. However, the present invention is not limited by the following Examples of compounds by any means.

EXAMPLE 1

Synthesis of 5′-(ethylsulfonyl)-6′-(5-methyl-1-(2,2,3,3,3-pentafluoropropyl)-1H-imidazol-4-yl)-2,3′-bipyridine (compound No. c-1)

(Step 1) Synthesis of 1-(5-bromo-3-(ethylthio)pyridin-2-yl)propan-1-one

5-Bromo-3-(ethylthio)picolinonitrile (1.0 g) was dissolved in diethyl ether (8.2 ml), the reaction system was purged with nitrogen, followed by cooling to −10° C. Ethylmagnesium bromide (1.0 M, tetrahydrofuran solution, 4.9 ml) was added dropwise thereto, and the mixture was stirred at −10° C. for 30 minutes, then heated to room temperature, and stirred at room temperature for 1 hour. 2 M Hydrochloric acid (10 ml) was added thereto, and the mixture was stirred at room temperature for 15 minutes. The obtained solution was adjusted to a pH of 8 with an aqueous solution of 2 M sodium hydroxide, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 1.2 g of the title compound (yield: quant.).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR(400 MHz, CDCl₃): δ 8.38 (d, 1H), 7.75 (d, 1H), 3.15 (q, 2H), 2.88 (q, 2H), 1.38 (t, 3H), 1.18 (t, 3H).

(Step 2) Synthesis of 1-(5-bromo-3-(ethylthio)pyridin-2-yl)propan-1-one oxime

1-(5-Bromo-3-(ethylthio)pyridin-2-yl)propan-1-one (0.50 g) was dissolved in ethanol (9.1 ml), and the solution was stirred at room temperature. Hydroxylamine hydrochloride (0.15 g) and sodium acetate (0.22 g) were added thereto, and the mixture was stirred at 60° C. for 7 hours. The obtained solution was poured to water, followed by extraction with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue (0.53 g) was used for the next step without being purified.

(Step 3) Synthesis of 1-(5-bromo-3-(ethylthio)pyridin-2-yl)propan-1-one O-tosvl oxime

The concentrate (containing 1-(5-bromo-3-(ethylthio)pyridin-2-yl)propan-1-one oxime) obtained from step 2 was dissolved in pyridine (5.5 ml), and the solution was stirred at room temperature. Paratoluenesulfonyl (0.52 g) was added thereto, and the mixture was stirred at room temperature for 18 hours. The obtained solution was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography to obtain 0.27 g of the title compound (yield: 34%, two steps).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR(400 MHz, CDCl₃): δ 8.42 (d, 1H), 7.82 (d, 2H), 7.77 (d, 1H), 7.31 (d, 2H), 2.92 (q, 2H), 2.59 (q, 2H), 2.44 (s, 3H), 1.29 (t, 3H), 1.07 (t, 3H).

(Step 4) Synthesis of 2-amino-1-(5-bromo-3-(ethylthio)pyridin-2-yl)propan-1-one

Sodium ethoxide (20%, ethanol solution, 0.084 g) was dissolved in ethanol (1.1 ml), and the solution was stirred at 0° C. An ethanol solution (1.2 ml) of 1-(5-bromo-3-(ethylthio)pyridin-2-yl)propan-1-one 0-tosyl oxime (0.10 g) was added dropwise thereto, and the mixture was stirred at room temperature for 3 hours. The obtained solution was filtered with celite. 2 M Hydrochloric acid (2.0 ml) was added to the obtained filtrate, and the mixture was stirred at room temperature for 30 minutes. The obtained solution was poured to water, followed by extraction with 1 M hydrochloric acid and water. The obtained aqueous layer was concentrated under reduced pressure to obtain 0.060 g of the title compound (yield: 92%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR(400 MHz, DMSO-d₆): δ 8.60 (d, 1H), 8.13 (d, 1H), 5.06 (m, 1H), 3.04 (q, 2H), 1.39 (d, 3H), 1.24 (t, 3H).

(Step 5) Synthesis of 4-(5-bromo-3-(ethylthio)pyridin-2-yl)-5-methyl-1,3-dihydro-2H-imidazole-2-thione

2-Amino-1-(5-bromo-3-(ethylthio)pyridin-2-yl)propan-1-one (0.10 g) was dissolved in toluene (3.5 ml), and the solution was stirred at room temperature. Potassium thiocyanate (0.17 g) and ammonium chloride (0.092 g) were added thereto, and the mixture was stirred at 110° C. for 4 hours. The solution was cooled to room temperature, the obtained solution was then poured to water, and the precipitated solid was filtered. The obtained solid was dried under reduced pressure to obtain 0.057 g of the title compound (yield: 50%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR(400 MHz, DMSO-d₆): δ 12.08 (brs, 1H), 11.99 (brs, 1H), 8.46 (d, 1H), 7.97 (d, 1H), 3.00 (q, 2H), 1.90 (s, 3H), 1.17 (t, 3H).

(Step 6) Synthesis of 5-bromo-3-(ethylthio)-2-(5-methyl-1H-imidazol-4-yl) pyridine

4-(5-Bromo-3-(ethylthio)pyridin-2-yl)-5-methyl-1,3-dihydro-2H-imidazole-2-thione (0.050 g) was suspended in water (1.4 ml), followed by stirring at room temperature. Nitric acid (0.15 ml) was added thereto, and the mixture was stirred at 110° C. for 1.5 hours. The solution was allowed to cool to room temperature, and the obtained solution was then poured to a 30% aqueous sodium hydroxide solution, followed by extraction with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate, and filtered. The obtained solution was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography to obtain 0.030 g of the title compound (yield: 66%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR(400 MHz, DMSO-d₆): δ 12.43 (brs, 1H), 8.70 (d, 1H), 8.26 (d, 1H), 7.69 (s, 1H), 3.29 (q, 2H), 2.52 (s, 3H), 1.08 (t, 3H).

(Step 7) Synthesis of 5-bromo-3-(ethylsulfonyl)-2-(5-methyl-1H-imidazol-4-yl)pyridine

5-Bromo-3-(ethylthio)-2-(5-methyl-1H-imidazol-4-yl)pyridine (0.10 g) was dissolved in a mixed solvent of dichloromethane (6.7 ml) and methanol (0.34 ml), and the solution was stirred at 0° C. m-Chloroperbenzoic acid (70%, 0.18 g) was added thereto, and the mixture was stirred at room temperature for 2 hours. The obtained solution was poured to a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate, followed by extraction with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate, and filtered. The obtained solution was concentrated under reduced pressure to obtain 0.11 g of the title compound (yield: 99%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR(400 MHz, DMSO-d₆): δ 12.28 (brs, 1H), 8.93 (d, 1H), 8.38 (d, 1H), 7.62 (s, 1H), 4.15 (q, 2H), 2.32 (s, 3H), 1.17 (t, 3H).

(Step 8) Synthesis of 5-bromo-3-(ethylsulfonyl)-2-(5-methyl-1-(2,2,3,3,3-pentafluoropropyl)-1H-imidazol-4-yl)pyridine

5-Bromo-3-(ethylsulfonyl)-2-(5-methyl-1H-imidazol-4-yl)pyridine (1.0 g) was dissolved in N,N-dimethylformamide (30 ml), and the solution was stirred at 0° C. 2,2,3,3,3-Pentafluoropropyl trifluoromethanesulfonate (1.3 g) and cesium carbonate (1.5 g) were added thereto, and the mixture was stirred at room temperature for 18 hours. The obtained solution was poured to a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The obtained solution was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography to obtain 1.1 g of the title compound (yield: 81%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR(400 MHz, CDCl₃): δ 8.85 (d, 1H), 8.57 (d, 1H), 7.54 (s, 1H), 4.48 (t, 2H), 3.95 (q, 2H), 2.37 (s, 3H), 1.33 (t, 3H).

(Step 9) Synthesis of 5′-(ethylsulfonyl)-6′-(5-methyl-1-(2,2,3,3,3-pentafluoropropyl)-1H-imidazol-4-yl)-2,3′-bipyridine

5-Bromo-3-(ethylsulfonyl)-2-(5-methyl-1-(2,2,3,3,3-pentafluoropropyl)-1H-imidazol-4-yl)pyridine (0.20 g) was dissolved in dioxane (4.3 ml), the reaction system was purged with nitrogen, followed by stirring at room temperature. Tributyl(2-pyridyl)tin (0.22 g), bis(triphenylphosphine)palladium (II) dichloride (0.030 g) and copper iodide (I) (0.016 g) were added thereto, and the mixture was stirred for 18 hours under heating to reflux. The obtained solution was poured to a saturated aqueous solution of potassium fluoride, and the mixture was filtered with celite. The obtained solution was extracted with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The obtained solution was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography to obtain 0.16 g of the title compound (yield: 78%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR(400 MHz, CDCl₃): δ 9.47 (d, 1H), 9.01 (d, 1H), 8.77-8.75 (m, 1H), 7.85-7.84 (m, 2H), 7.57 (s, 1H), 7.36-7.32 (m, 1H), 4.50 (t, 2H), 3.96 (q, 2H), 2.41 (s, 3H), 1.35 (t, 3H). [0242]

EXAMPLE 2

Synthesis of (Z)-5-cyclopropyl-3-(ethylsulfonyl)-2-(1-(2,3,3,4,4,5,5,5-octafluoropent-1-en-1-yl)-1H-1,2,4-triazol-3-yl)pyridine (compound No. b-1)

(Step 1) Synthesis of 5-bromo-3-(ethylthio)picolinonitrile

5-Bromo-3-nitropicolinonitrile (1 g) was dissolved in tetrahydrofuran (22 ml), the reaction vessel was purged with nitrogen, followed by cooling to −5° C. and stirring. Ca. 60% sodium hydride (0.2 g) was added thereto, the mixture was stirred for 5 minutes, ethylmercaptan (0.27 g) was then added dropwise, and the mixture was stirred at −5° C. for 30 minutes. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.90 g of the title compound (yield: 84%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 7.83 (1H, d), 3.07 (2H, q), 1.41 (3H, t).

(Step 2) Synthesis of 5-bromo-3-(ethylsulfonyl) picolinonitrile

5-Bromo-3-(ethylthio)picolinonitrile (149 g) was dissolved in dichloromethane (1800 ml), and the solution was cooled to 0° C. and stirred. 70% m-chloroperbenzoic acid (333 g) was added thereto, and the mixture was stirred overnight at room temperature. The obtained solution was poured to a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate, followed by extraction with dichloromethane. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 167 g of the title compound (yield: 99%). ¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 9.26 (1H, d), 8.72 (1H, d), 3.60 (2H, q), 1.23 (3H, t).

(Step 3) Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)picolinonitrile

5-Bromo-3-(ethylthio)picolinonitrile (1.0 g) was dissolved in xylene (16 ml), the reaction vessel was purged with argon, and the solution was then stirred at room temperature. Potassium cyclopropyl trifluoroborate (1.3 g), palladium acetate (II) (0.16 g), a solution of 20% tricyclohexylphosphine in toluene (2.0 g), tripotassium phosphate (4.1 g), and water (2 ml) were added thereto, and the mixture was stirred overnight at 110° C. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.75 g of the title compound (yield: 89%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 7.94 (1H, d), 3.45 (2H, q), 2.10-2.03 (1H, m), 1.37 (3H, t), 1.35-1.30 (2H, m), 0.98-0.94 (2H, m).

(Step 4) Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)picolinamide

5-Cyclopropyl-3-(ethylsulfonyl)picolinonitrile (0.75 g) was dissolved in acetone (45 ml), and the solution was cooled to 0° C. An aqueous solution of 2 M sodium hydroxide (6.5 ml) and 30% hydrogen peroxide water (5 ml) were added dropwise thereto, and the mixture was stirred overnight at room temperature. The obtained solution was poured to a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.69 g of the title compound (yield: 85%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.51 (1H, d), 8.09 (1H, d), 5.73 (2H, br s), 3.88 (2H, q),2.09-2.02 (1H, m), 1.33 (3H, t), 1.24-1.19 (2H, m), 0.92-0.88 (2H, m).

(Step 5) Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)-2-(1H-1,2,4-triazol-3-yl)pyridine

N,N-Dimethylformamide dimethyl acetal (11 ml) was added to 5-cyclopropyl-3-(ethylsulfonyl)picolinamide (0.69 g), and the mixture was stirred for 1 hour under heating to reflux. The obtained solution was concentrated under reduced pressure, acetic acid (14 ml) and hydrazine monohydrate (0.16 g) were added to the obtained residue, and the mixture was stirred at 90° C. for 1 hour. The obtained solution was concentrated under reduced pressure, and neutralized with a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.69 g of the title compound (yield: 85%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 12.21 (1H, br s), 8.65 (1H, d), 8.19 (1H, s), 8.12 (1H, d), 3.96 (2H, q), 2.11-2.03 (1H, m), 1.33 (3H, t), 1.25-1.20 (2H, m), 0.94-0.90(2H, m).

(Step 6) Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)-2-(1-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-1H-1,2,4-triazol-3-yl)pyridine (compound No. b-2)

Ca. 55% sodium hydride (0.05 g) was suspended in N,N-dimethylformamide (10 ml), followed by stirring at 0° C. 5-Cyclopropyl-3-(ethylsulfonyl)-2-(1H-1,2,4-triazol-3-yl)pyridine (0.27 g) was added thereto, and the mixture was stirred at 0° C. for 30 minutes. 2,2,3,3,4,4,5,5,5-nonafluoropentyl trifluoromethanesulfonate (0.44 g) prepared by the method described in WO2005/063694 was added dropwise thereto, and the mixture was stirred overnight at room temperature. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.27 g of the title compound (yield: 56%)

¹H-NMR and ¹⁹F-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.72 (1H, d), 8.31 (1H, s), 8.05 (1H, d), 4.95 (2H, t), 3.83 (2H, q), 2.10-2.04 (1H, m), 1.35 (3H, t), 1.23-1.18 (2H, m), 0.92-0.88 (2H, m); ¹⁹F-NMR (376 MHz, CDCl₃-C₆F₆): δ −81.30 (3F, tt), −117.42-117.60 (2F, m), −124.24-124.40 (2F, m), −126.34-136.49 (2F, m).

(Step 7) Synthesis of (Z)-5-cyclopropyl-3-(ethylsulfonyl)-2-(1-(2,3,3,4,4,5,5,5-octafluoropent-1-en-1-yl)-1H-1,2,4-triazol-3-yl)pyridine

5-Cyclopropyl-3-(ethylsulfonyl)-2-(1-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-1H-1,2,4-triazol-3-yl)pyridine (0.24 g) was dissolved in tetrahydrofuran (9 ml), and the solution was stirred at room temperature. An aqueous solution of 2 M sodium hydroxide (1.2 ml) was added dropwise thereto, and the mixture was stirred overnight at 60° C. The obtained solution was poured a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.14 g of the title compound (yield: 62%).

¹H-NMR and ¹⁹F-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.73 (1H, d), 8.72 (1H, d), 8.05 (1H, d), 7.41 (1H, d), 3.87 (2H, q), 2.12-2.05 (1H, m), 1.37 (3H, t), 1.25-1.20 (2H, m), 0.94-0.90 (2H, m); ¹⁹F-NMR (376 MHz, CDCl₃—C₆F₆): δ −81.01 (3F, t), −119.28-119.39 (2F, m), −127.35-127.40 (2F, m), −133.46-133.70 (1F, m).

EXAMPLE 3 Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)-2-(1-(5-(trifluoromethyl)pyridin-2-yl)-1H-1,2,4-triazol-3-yl)pyridine (compound No. d-4) (Step 1) Synthesis of 5-bromo-3-(ethylsulfonyl)picolinamide

5-Bromo-3-(ethylsulfonyl)picolinonitrile (1.0 g) was dissolved in acetone (50 ml), and the solution was cooled to 0° C. An aqueous solution of 2 M sodium hydroxide (8.0 ml) and 30% hydrogen peroxide water (6.0 ml) were added dropwise thereto, and the mixture was stirred overnight at room temperature. The obtained solution was poured to a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.93 g of the title compound (yield: 88%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.82 (1H, d), 8.68 (1H, d), 7.16 (1H, br s), 5.78 (1H, br s), 3.90 (2H, q), 1.36 (3H, t).

(Step 2) Synthesis of 5-bromo-3-(ethylsulfonyl)-2-(1H-1,2,4-triazol-3-yl)pyridine

N,N-Dimethylformamide dimethyl acetal (13 ml) was added to 5-bromo-3-(ethylsulfonyl)picolinamide (0.93 g), and the mixture was stirred for 1 hour under heating to reflux. The obtained solution was concentrated under reduced pressure, and acetic acid (16 ml) and hydrazine monohydrate (0.19 g) were added to the obtained residue, and the mixture was stirred at 90° C. for 1 hour. The obtained solution was concentrated under reduced pressure, and neutralized with a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.53 g of the title compound (yield: 52%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 11.72 (1H, br s), 8.95 (1H, d), 8.72 (1H, d), 8.24 (1H, s), 4.03 (2H, q), 1.37 (3H, t).

(Step 3) Synthesis of 5-bromo-3-(ethylsulfonyl)-2-(1-(5-(trifluoromethyl)pyridin-2-yl)-1H-1,2,4-triazol-3-yl)pyridine

Ca. 55% sodium hydride (0.084 g) was suspended in N,N-dimethylformamide (16 ml), followed by stirring at 0° C. 5-Bromo-3-(ethylsulfonyl)-2-(1H-1,2,4-triazol-3-yl)pyridine (0.50 g) was added thereto, and the mixture was stirred at 0° C. for 30 minutes. 2-Chloro-5-(trifluoromethyl)pyridine (0.34 g) was added thereto, and the mixture was stirred at 100° C. for 4 hours. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.22 g of the title compound (yield: 29%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 9.32 (1H, s), 9.05 (1H, d), 8.78 (1H, s), 8.67 (1H, d), 8.18-8.10 (2H, m), 3.98 (2H, q), 1.43 (3H, t).

(Step 4) Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)-2-(1-(5-(trifluoromethyl)pyridin-2-yl)-1H-1,2,4-triazol-3-yl)pyridine

5-Bromo-3-(ethylsulfonyl)-2-(1-(5-(trifluoromethyl)pyridin-2-yl)-1H-1,2,4-triazol-3-yl)pyridine (0.11 g) was dissolved in xylene (2.2 ml), and the reaction vessel was purged with argon, followed by stirring at room temperature. Potassium cyclopropyl trifluoroborate (0.089 g), palladium acetate (II) (0.011 g), a solution of 20% tricyclohexylphosphine in toluene (0.13 g), tripotassium phosphate (0.27 g) and water (0.22 ml) were added thereto, and the mixture was stirred overnight at 110° C. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.075 g of the title compound (yield: 74%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 9.30 (1H, s), 8.76 (1H, s), 8.75 (1H, d), 8.16-8.11 (2H, m),8.08 (1H, d), 3.93 (2H, q), 2.13-2.06 (1H, m), 1.39 (3H, t), 1.28-1.20 (2H, m), 0.95-0.90 (2H, m).

EXAMPLE 4 Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)-2-(1-(4-(trifluoromethoxy)phenyl)-1H-imidazol-4-yl)pyridine (compound No. d-19) (Step 1) Synthesis of 2-bromo-1-(5-bromo-3-(ethylthio)pyridin-2-yl) ethan-1-one

1-(5-Bromo-3-(ethylthio)pyridin-2-yl)ethan-1-one (1.95 g) was dissolved in tetrahydrofuran (40 ml), phenyltrimethylammonium tribromide was then added, and the mixture was stirred overnight at 50° C. The obtained solution was poured to a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 1.02 g of the title compound (yield: 40%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.41 (1H, d), 7.80 (1H, d), 4.77 (2H, s), 2.93 (2H, q), 1.42 (3H, t).

(Step 2) Synthesis of 1-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-((4-(trifluoromethoxy)phenyl)amino)ethan-1-one

2-Bromo-1-(5-bromo-3-(ethylthio)pyridin-2-yl)ethan-1-one (1.36 g) was dissolved in N,N-dimethylformamide (20 ml), and the solution was cooled to 0° C. and stirred. 4-(Trifluoromethoxy)aniline (0.78 g) and potassium carbonate (0.66 g) were added thereto, and the mixture was stirred at room temperature for 3 hours. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was washed with hexane to obtain 1.46 g of the title compound (yield: 83%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.82 (1H, d), 7.06 (2H, d), 6.67 (2H, d), 4.94-4.87 (1H, brs), 4.75 (2H, d), 2.95 (2H, q), 1.43 (3H, t).

(Step 3) Synthesis of 4-(5-bromo-3-(ethylthio)pyridin-2-yl)-1-(4-(trifluoromethoxy)phenyl)-1,3-dihydro-2H-imidazole-2-thione

1-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-((4-(trifluoromethoxy)phenyl)amino)ethan-1-one (1.46 g) was dissolved in acetic acid (10 ml). Potassium thiocyanate (0.65 g) was added thereto, and the mixture was stirred at 100° C. for 30 minutes. The obtained solution was concentrated under reduced pressure, and neutralized with a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was washed with diethyl ether to obtain 0.66 g of the title compound (yield: 41%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 10.30-10.19 (1H, br), 8.45 (1H, d), 7.83 (1H, d), 7.79-7.74 (3H, m), 7.40-7.35 (2H, m), 3.07 (2H, q), 1.40 (3H, t).

(Step 4)

Synthesis of 5-bromo-3-(ethylsulfinyl)-2-(1-(4-(trifluoromethoxy)phenyl)-1H-imidazol-4-yl)pyridine

4-(5-Bromo-3-(ethylthio)pyridin-2-yl)-1-(4-(trifluoromethoxy)phenyl)-1,3-dihydro-2H-imidazole-2-thione (0.66 g) was suspended in water (9 ml). Fuming nitric acid (1 ml) was added thereto, and the mixture was stirred for 1 hour under heating to reflux. The obtained solution was neutralized with a 25% aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was used for the next step without being purified.

(Step 5) Synthesis of 5-bromo-3-(ethylsulfonyl)-2-(1-(4-(trifluoromethoxy)phenyl)-1H-imidazol-4-yl)pyridine

The 5-bromo-3-(ethylsulfinyl)-2-(1-(4-(trifluoromethoxy)phenyl)-1H-imidazol-4-yl)pyridine obtained from step 4 was dissolved in dichloromethane, and the solution was stirred at 0° C. m-Chloroperbenzoic acid (70%, 0.37 g) was added thereto, and the mixture was stirred at room temperature for 1 hour. The obtained solution was poured to a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate, followed by extraction with dichloromethane. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.56 g of the title compound (yield: 35%, two steps).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.85 (1H, d), 8.64 (1H, d), 8.00 (1H, d), 7.91 (1H, d), 7.54-7.48 (2H, m), 7.42-7.35 (2H, m), 4.00 (2H, q), 1.35 (3H, t).

(Step 6) Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)-2-(1-(4-(trifluoromethoxy)phenyl)-1H-imidazol-4-yl)pyridine

5-Bromo-3-(ethylsulfonyl)-2-(1-(4-(trifluoromethoxy)phenyl)-1H-imidazol-4-yl)pyridine (0.13 g) and toluene (4 ml) were added to a microwave synthesis reaction vessel. Cyclopropylboronic acid (0.070 g), palladium acetate (II) (0.0070 g), tri(o-tolyl)phosphine (0.018 g), potassium carbonate (0.11 g) and water (0.5 ml) were added thereto, and the mixture was reacted at 120° C. for 1 hour using a microwave synthesis apparatus. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography to obtain 0.080 g of the title compound (yield: 67%).

¹H-NMR of the obtained title compound will be shown below.

¹H-NMR (CDCl₃) δ: 8.62 (1H, d), 8.08 (1H, d), 7.93 (1H, d), 7.90 (1H, d), 7.54-7.48 (2H, m), 7.40-7.34 (2H, m), 3.84 (2H, q), 2.07-1.99 (1H, m), 1.30 (3H, t), 1.19-1.12 (2H, m), 0.90-0.83 (2H, m).

Examples of the heteroaryl azole compounds of the present invention produced in the same way as in Examples described above are shown in Tables 1 to 4. Table 1 shows the substituents of the compound of formula (I-1). Table 2 shows the substituents of the compound of formula (III-1). The physical property data of the compounds is described in the columns of “physical properties”. Properties or melting points (m.p.) are described as physical property data. When R is a substituted or unsubstituted C1-6 alkenyl group, the configuration of the double bond of the C1-6 alkenyl group is described in the column of “conformation”. “E” represents an E-configuration, “Z” represents a Z-configuration, and “E/Z” means that the compound is a mixture of compounds of E- and Z-configurations.

In the tables, Me represents a methyl group, Et represents an ethyl group, and ^(c)Pr represents a cyclopropyl group.

TABLE 1 Compound No. R¹ R² R³ R (X)_(n) Conformation Physical properties. a-1 SO₂Et Me H CH═C(F)CF₂CF₂CF₃ 5-CF₃ Z m.p.: 147-149(° C.) a-2 SO₂Et Me H CH₂CF₂CF₂CF₂CF₃ 5-CF₃ — m.p.: 111-113(° C.) a-3 SO₂Et Me H CH═C(F)CHFCF₃ 5-^(c)Pr Z m.p.: 173-176(° C.) a-4 SO₂Et Me H CH═C(F)CF₂CF₃ 5-CF₃ Z m.p.: 159-161(° C.) a-5 SO₂Et Me H CH₂CF₂CF₃CF 

  5-CF₃ — m.p.: 109-111(° C.) a-6 SO₂Et Me H CH═C(F)CF₂CF 

 CF₂ — Z m.p.: 179-181(° C.) a-7 SO₂Et Me H CH═C(F)CF₂CF 

  — Z m.p.: 193-195(° C.) a-8 SO₂Et Me H CH₂CF₂CF₂CF₂CF₃ — — m.p.: 64-65(° C.) a-9 SO₂Et Me H CH₂CF₂CF₂CF₃ — — m.p.: 100-102(° C.) a-10 SO₂Et Me H CH₂CF₂CHFCF₃ 5-^(c)Pr — m.p.: 116-118(° C.) a-11 SO₂Et Me H CH═C(F)CF₃ — Z m.p.: 213-215(° C.) a-12 SO₂Et Me H CH₂CF₃CF₃ — — m.p.: 96-98(° C.) a-13 SO₂Et Me H CH═C(F)CF₂CF₃ 5-^(c)Pr Z m.p.: 155-157(° C.) a-14 SO₂Et Me H CH═C(F)CF₃ 5-^(c)Pr Z m.p.: 163-165(° C.) a-15 SO₂Et Me H CH₂CF₃CF₂CF₂CHF₂ 5-(pyrimidin-2-yl) — m.p.: 112-114(° C.) a-16 SO₂Et Me H CH₂CF₂CF₃CF₂ 5-(pyridin-2-yl) — m.p.: 183-185(° C.) a-17 SO₂Et Me H CH═C(F)CF₂CF₃ 6-(1H-1,2,4-triazol-1-yl) Z m.p.: 182-184(° C.) a-18 SO₂Et Me H CF═CHFOCF₂CF₂CF₃ 5-CF₃ E/Z amorphous a-19 SO₂Et Me H CF₂CHFOCF₂CF₂CF₃ 5-CF₃ — viscous oil

indicates data missing or illegible when filed

TABLE 2 Compound No. R¹ R³ R (X)_(n) Conformation Physical properties. b-1 SO₂Et H CH═C(F)CF₂CF₂CF₃ 5-^(c)Pr Z m.p. 102-104(° C.) b-2 SO₂Et H CH₂CF₂CF₂CF₂CF₃ 5-^(c)Pr — m.p.: 190-193(° C.) b-3 SO₂Et H CH═C(F)CF₂CF₃ 5-(3,5-F₂-phenyl) Z m.p.: 138-140(° C.) b-4 SO₂Et H CH═C(F)CF₃ — Z m.p.: 155-157(° C.) b-5 SO₂Et H CH═C(F)CF₃CF₂CF₃ — Z m.p.: 144-146(° C.) b-6 SO₂Et H CH₂CF₂CF₃ — — m.p.: 112-115(° C.) b-7 SO₂Et H CH₂CF₂CF₂CF₂CF₃ — — m.p.: 135-137(° C.) b-8 SO₂Et H CH═C(F)CF₂CF₃ — Z m.p.: 152-154(° C.) b-9 SO₂Et H CH₂CF₂CF₂CF₃ — — m.p.: 137-138(° C.) b-10 SO₂Et H CH═C(F)CF₂CF₃ 5-^(c)Pr Z m.p.: 102-104(° C.) b-11 SO₂Et H CH 

 CF₂CF₂CF₃ 5-^(c)Pr — m.p.: 180-182(° C.) b-12 SO₂Et H CH═C(F)CF₂CF₃ 5-(pyrimidin-2-yl) Z m.p.: 255-260(° C.) b-13 SO₂Et H CH₂CF₂CF 

 CF₃ 5-(pyrimidin-2-yl) — m.p.: 261-265(° C.) b-14 SO₂Et H CH₂CF₂CF 

 CF₃ 5-Br — m.p.: 205-207(° C.) b-15 SO₂Et H CH₂CF₂CF 

 CF₃ 6-(ethylsulfonyl) — m.p.: 211-213(° C.) b-16 SO₂Et H CH₂CF₂CF₃CF 

  6-(1H-1,2,4-triazol-1-yl) — m.p.: 244-246(° C.) b-17 SO₂Et H CH═C(F)CF₂CF₃ 6-(1H-1,2,4-triazol-1-yl) Z m.p.: 202-204(° C.) b-18 SO₂Et H CH₂CF₂CF₂CF₂CF₃ 6-(1H-1,2,4-triazol-1-yl) — m.p.: 242-246(° C.) b-19 SO₂Et H CH═C(F)CF₂CF₂CF₃ 6-(1H-1,2,4-triazol-1-yl) Z m.p.: 200-202(° C.) b-20 SO₂Et H CH═C(F)CF₂CF₂CHF₂ 5-Br Z m.p.: 118-120(° C.) b-21 SO₂Et H CH═C(F)CF₂CF₂CHF₂ 5-^(c)Pr Z viscous oil b-22 SO₂Et H CH═C(F)CF₂CF₂CF₂ 5-(1-Me-^(c)Pr) Z m.p.: 144-146(° C.) b-23 SO₂Et H CF₂CHFOCF₂CF₂CF₃ 5-^(c)Pr — viscous oil b-24 SO₂Et H CF₂CHFOCF₃ 5-(pyrimidin-2-yl) — m.p.: 110-114 b-25 SO₂Et H CF₂CHFOCF₃ 5-^(c)Pr — n 

  (19.7° C.); 1.491

indicates data missing or illegible when filed

TABLE 3 Compound No. Structure Physical properties. c-1

m.p.: 151-153 (° C.) c-2

m.p.: 142-144 (° C.) c-3

m.p.: 120-122 (° C.) c-4

amorphous c-5

m.p.: 97-99 (° C.) c-6

m.p.: 113-115 (° C.) c-7

m.p.: 98-100 (° C.) c-8

m.p.: 208-210 (° C.) c-9

m.p.: 243-245 (° C.) c-10

m.p.: 118-120 (° C.) c-11

m.p.: 132-135 (° C.)

TABLE 4-1 Compound No. Structure Physical properties. d-1

PALE YELLOW SOLID d-2

m.p.: 152-155 (° C.) d-3

m.p.: 196-199 (° C.) d-4

m.p.: 193-195 (° C.) d-5

m.p.: 248-250 (° C.) d-6

m.p.: 232-234 (° C.) d-7

m.p.: 110-112 (° C.) d-8

m.p.: 135-139 (° C.) d-9

m.p.: 146-148 (° C.) d-10

m.p.: 72-74 (° C.)

TABLE 4-2 d-11

m.p.: 226-228 (° C.) d-12

m.p.: 106-108 (° C.) d-13

m.p.: 88-90 (° C.) d-14

m.p.: 113-115 (° C.) d-15

m.p.: 142-144 (° C.) d-16

m.p.: 204-206 (° C.) d-17

m.p.: 162-164 (° C.) d-18

m.p.: 245-247 (° C.) d-19

m.p.: 120-122 (° C.) d-20

m.p.: 199-201 (° C.)

TABLE 4-3 d-21

m.p.: 208-210 (° C.) d-22

m.p.: 185-187 (° C.) d-23

m.p.: 165-167 (° C.) d-24

m.p.: 161-163 (° C.) d-25

m.p.: 152-154 (° C.) d-26

m.p.: 198-200 (° C.) d-27

m.p.: 236-238 (° C.)

The ¹H-NMR data of compounds having physical properties of viscous oil or amorphous among the compounds shown in Tables 1 to 3 will be shown below.

Compound No. (a-18): ¹H-NMR(400 MHz, CDCl₃): δ 9.06 (1H, s), 8.71 (1H, s), 7.59 (1H, s), 4.05 (2H, q), 2.49 (3H, s), 1.38 (3H, t).

Compound No. (a-19): ¹H-NMR(400 MHz, CDCl₃): δ 9.09 (1H, s), 8.71 (1H, s), 7.74 (1H, s), 6.40 (1H, d), 3.97 (2H, q), 2.50 (3H, s), 1.36 (3H, t).

Compound No. (b-21): ¹H-NMR(400 MHz, CDCl₃): δ 8.72 (2H, dd), 8.05 (1H, d), 7.38 (1H, d), 6.10 (1H, tt), 3.88 (2H, q), 2.12-2.04 (1H, m), 1.37 (3H, t), 1.30-1.16 (2H, m), 0.96-0.87 (2H, m).

Compound No. (b-23): ¹H-NMR(400 MHz, CDCl₃): δ 8.73 (1H, d), 8.62 (1H, s), 8.06 (1H, d), 6.65 (1H, ddd), 3.76 (2H, q), 2.12-2.05 (1H, m), 1.36 (3H, t), 1.26-1.21 (2H, m), 0.93-0.89 (2H, m).

Compound No. (c-4): ¹H-NMR(400 MHz, CDCl₃): δ 8.85 (d, 1H), 8.57 (d, 1H), 7.54 (s, 1H), 4.48 (t, 2H), 3.95 (q, 2H), 2.37 (s, 3H), 1.33 (t, 3H).

[Biological Test]

Test Examples given below show that the heteroaryl azole compound of the present invention is useful as an active ingredient for pest control agents and ectoparasite control agents. The term “part” is based on weight.

(Preparation of Test Emulsion)

5 parts of the heteroaryl azole compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare emulsion (I) containing 5% of the active ingredient.

For a control, 98.5 parts of dimethylformamide and 1.5 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare emulsion (II).

An insecticidal rate was calculated according to the following expression:

Insecticidal rate (%)=(The number of dead insects/The number of tested insects)×100

Test Example 1 Test of efficacy on Mythimna separata

0.8 g of commercially available artificial feed (Insecta LFS, manufactured by Nosan Corp.) and 1 μl of the emulsion (I) were well mixed to obtain test feed.

A plastic test container (capacity: 1.4 ml) was packed with 0.2 g of the test feed per treatment plot. Then, two second instar larvae of Mythimna separata were inoculated to each treatment plot. A plastic lid was put on the test container so as to prevent escape of the second instar larvae of Mythimna separata. The container was placed in a thermostat chamber of 25° C. On the fifth day, the insecticidal rate and the food intake were examined. The test was conducted in duplicate.

The insecticidal rate and the food intake of a control plot were examined in the same way as in Test Example 1 except that the emulsion (I) was changed to the emulsion (II).

Compounds of compound Nos. a-4, a-5, a-14, a-15, a-16, a-17, b-3, b-10, b-12, b-20, b-22, c-1, c-2, c-5, c-6, d-3, d-4, d-5, d-6, d-9, d-10, d-11, d-13, d-14, d-15, d-16, d-19, d-20, d-24, d-25, d-26, and d-27 were tested for their efficacy on Mythimna separata. All the compounds had an insecticidal rate of 100% for Mythimna separata or a food intake of 10% or less as compared with the control plot. As is evident, the heteroaryl azole compound of the present invention is effective for Mythimna separata.

Test Example 2 Test of efficacy on Plutella xylostella

The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were dipped in the dilution for 30 seconds. The resulting cabbage leaves were placed in a petri dish. Five second instar larvae of Plutella xylostella were released thereto. The petri dish was placed in a thermostat chamber having a temperature of 25° C. and a humidity of 60%. Life and death were determined after 3 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

Compounds of compound Nos. a-3, a-4, a-13, a-14, a-15, a-16, a-17, b-3, b-10, b-12, b-21, b-22, b-25, c-5, c-8, c-9, d-1, d-4, d-5, d-6, d-7, d-15, d-16, d-19, d-20, d-22, d-23, d-24, d-25, d-26 and d-27 were tested for their efficacy on Plutella xylostella. All the compounds exhibited an insecticidal rate of 80% or more for Plutella xylostella.

Test Example 3 Test of efficacy on Aphis craccivora

Seedlings of black-eyed peas were raised in 10-cm pots. Aphis craccivora nymphs were inoculated onto primary leaves. The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm. The dilution was sprayed to the black-eyed peas parasitized by the Aphis craccivora nymphs. The black-eyed peas were placed in a thermostat chamber having a temperature of 25° C. and a humidity of 60%. Life and death of Aphis craccivora were determined after 4 days from the spraying, and the insecticidal rate was calculated. The test was conducted in duplicate.

Compounds of compound Nos. a-4, a-5, a-6, a-7, a-8, a-9, a-10, a-14, a-15, a-16, a-17, b-3, b-4, b-5, b-8, b-10, b-12, b-13, b-14, b-20, b-22, b-23, b-24, b-25, c-1, c-2, c-3, c-4, c-5, c-6, c-7, d-3, d-4, d-6, d-10, d-11, d-14, d-16, d-18, d-19, d-20, d-21, d-22, d-24, d-25, d-26, and d-27 were tested for their efficacy on Aphis craccivora. All the compounds exhibited an insecticidal rate of 80% or more for Aphis craccivora.

Test Example 4 Test of efficacy on Phyllotreta striolata

The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm to prepare a test chemical. The test chemical was sprayed to Qing geng cai seedlings (at the seventh true leaf stage) planted in 10-cm pots. The Qing geng cai seedlings were dried in air and then placed in a plastic cup. Ten Phyllotreta striolata adults were released thereto. The plastic cup was stored in a thermostat chamber having a temperature of 25° C. and a humidity of 65%. Life and death were determined after 7 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

Compounds of compound Nos. a-3, a-13, a-14, b-3, b-8, b-10, b-12, b-13, c-5, c-8, c-9, d-1, d-6, d-7, d-19, d-20, and d-22 were tested for their efficacy on Phyllotreta striolata adults. All the compounds exhibited an insecticidal rate of 80% or more for Phyllotreta striolata adults.

Test Example 5 Test of efficacy on Nilaparvata lugens

The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm. Young seedlings of rice were dipped in the dilution for 30 seconds. The young seedlings of rice were dried in air and then placed in a plastic case. Five second instar larvae of Nilaparvata lugens were released thereto. The plastic case was stored in a thermostat chamber having a temperature of 25° C. and a humidity of 65%. Life and death were determined after 7 days from the inoculation, and the insecticidal rate was calculated. The test was conducted in duplicate.

Compounds of compound Nos. a-3, a-4, a-13, a-17, c-8, c-9 and d-25 were tested for their efficacy on Nilaparvata lugens. All the compounds exhibited an insecticidal rate of 80% or more for Nilaparvata lugens.

All the compounds selected at random from among the heteroaryl azole compounds of the present invention exerted the effect as described above. It may therefore be understood that the heteroaryl azole compound of the present invention, including unillustrated compounds, is a compound having an effect such as a pest control effect, particularly, a miticidal or insecticidal effect. It may also be understood that the heteroaryl azole compound of the present invention is a compound also having an effect on parasites harmful to humans and animals, such as ectoparasites. 

1. A compound of formula (II), an N-oxide compound, stereoisomer, tautomer or hydrate thereof, or a salt of any of these compounds:

wherein R¹ represents a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group or a substituted or unsubstituted C1-6 alkylsulfonyl group; B¹ represents a nitrogen atom or CR²; R² represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted amino group, a cyano group or a halogeno group; R³ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group; R represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group; A represents a carbon atom or a nitrogen atom; X represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group; n represents a number of chemically acceptable X, and is an integer of 0 to 2; and X is the same or different when n is
 2. 2. The compound according to claim 1, an N-oxide compound, stereoisomer, tautomer or hydrate thereof, or a salt of any of these compounds, wherein in the formula (II), R represents a C1-6 haloalkyl group, a C1-6 haloalkoxy C1-6 haloalkyl group, a C2-6 haloalkenyl group or a C1-6 haloalkoxy C2-6 haloalkenyl group.
 3. The compound according to claim 1, an N-oxide compound, stereoisomer, tautomer or hydrate thereof, or a salt of any of these compounds, wherein formula (II) is formula (IV):

wherein R¹′ represents a substituted or unsubstituted C1-6 alkylsulfonyl group; B¹′ represents a nitrogen atom or CR²′; R² represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted amino group, a cyano group or a halogeno group; R³′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group; R′ represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group; B²′ represents a nitrogen atom or CX¹′; X¹′ represents a hydrogen atom, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group or a cyano group; and X²′ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group, with the proviso that both X¹ and X² are not hydrogen atoms at the same time.
 4. A pest control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 5. An insecticide or acaricide comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 6. An ectoparasite control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 7. An endoparasite control agent or expellant comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 8. A pest control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 9. A pest control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 3, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 10. An insecticide or acaricide comprising at least one active ingredient selected from the group consisting of a compound according to claim 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 11. An insecticide or acaricide comprising at least one active ingredient selected from the group consisting of a compound according to claim 3, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 12. An ectoparasite control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 13. An ectoparasite control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 3, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 14. An endoparasite control agent or expellant comprising at least one active ingredient selected from the group consisting of a compound according to claim 2, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 15. An endoparasite control agent or expellant comprising at least one active ingredient selected from the group consisting of a compound according to claim 3, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds. 